19748-66-4|3-(1-Pyrrolidyl)-1-propanol| Ambeed

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Quality Control of [ 19748-66-4 ] Purity: 95% SDS Specification

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Product Details of [ 19748-66-4 ]

CAS No. :	19748-66-4
Formula :	C₇H₁₅NO
M.W :	129.20
SMILES Code :	OCCCN1CCCC1
MDL No. :	MFCD01687769
InChI Key :	ZMJQROKRSPSLFH-UHFFFAOYSA-N
Pubchem ID :	209342

Safety of [ 19748-66-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 19748-66-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	41.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.47 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.98
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.42
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.08
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.57
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.09
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.83

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.71
Solubility	25.3 mg/ml ; 0.196 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.48
Solubility	42.8 mg/ml ; 0.331 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.93
Solubility	15.3 mg/ml ; 0.119 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.79 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.07

Application In Synthesis of [ 19748-66-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 19748-66-4 ]

[ 19748-66-4 ] Synthesis Path-Downstream 1~35

1
[ 123-75-1 ]
[ 627-30-5 ]
[ 19748-66-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate; In acetonitrile;	The starting material was prepared as follows: Pyrrolidine (50 g, 700 mmol), 3-chloropropanol (58.5 ml, 700 mmol) and potassium carbonate (145 g, 1.05 mol) were refluxed in acetonitrile (1 l) for 20 hours. Upon cooling to ambient temperature the precipitate was filtered off and rinsed with acetonitrile. The solvent was evaporated off and the residual oil purified by distillation under vacuum to give 3-(pyrrolidin-1-yl)propan-1-ol (62.1 g, 69%). 1H NMR Spectrum: (CDCl3) 1.75 (m, 6H); 2.55 (m, 4H); 2.75 (t, 2H); 3.85 (t, 2H); 5.50 (br s, (1H)
69%	With potassium carbonate; In acetonitrile;	Pyrrolidine (50 g, 700 mmol), 3-chloropropanol (58.5 ml, 700 mmol) and potassium carbonate (145 g, 1.05 mol) were refluxed in acetonitrile (1 l) for 20 hours. Upon cooling to ambient temperature the precipitate was filtered off and rinsed with acetonitrile. The solvent was evaporated off and the residual oil purified by distillation under vacuum to give 3-(pyrrolidin-1-yl)propan-1-ol (62.1 g, 69%). 1H NMR Spectrum: (CDCl3) 1.75 (m, 6H); 2.55 (m, 4H); 2.75 (t, 21); 3.85 (t, 2H); 5.50 (br s,
	In acetonitrile; for 20h;Heating / reflux;	A solution of pyrrolidine (50 g, 0.7 mol) and 3-chloropropan-1-ol (66.15 g, 0.7 mol) in acetonitrile (11) containing potassium carbonate (145 g, 1.05 mol) was refluxed for 20 hours. After cooling, the mixture was filtered, the solid was washed with acetonitrile and the filtrate was evaporated. The residue was distilled at about 130C under about 70 mmHg to give 1-(3-hydroxypropyl)pyrrolidine (62.1 g, 69%). MS-ESI: 130 [MH]+ 1H NMR Spectrum: (CDCl3) 1.6-1.8 (m, 6H); 2.55 (br s, 4H); 2.75 (t, 2H); 3.85 (t, 2H); 5.2-5.8 (br s, 1H)

	With potassium carbonate; In acetonitrile; for 20h;Heating / reflux;	The N-(3-hydroxypropyl)pyrrolidine used as a starting material was prepared as follows: A mixture of 3-chloropropanol (66 g), pyrrolidine (50 g), potassium carbonate (145 g) and acetonitrile (1 L) was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was purified by distillation to give the required starting material as an oil (62 g); NMR Spectrum: (CDCl3) 1.6-1.8 (m, 6H), 2.55 (br s, 4H), 2.75 (t, 2H), 3.85 (t, 2H), 5.5 (br s, 1H).
	With sodium hydroxide; In water; at 25 - 70℃;	tert-Butyl 4-(pyridin-3-yl)-4-(3-(pyrrolidin-1-yl)propoxy)piperidine-1-carboxylate AM-05 Stage 1. First pyrrolidine (6.95 ml) and then 3-chloropropanol (10 g, 106.3 mmol) were slowly added to a solution, heated to 50 C., of NaOH (5.06 g, 126.5 mmol) in water (4.55 ml) such that the solution did not heat up to above 70 C. After the complete addition, the mixture was first stirred at this temperature for a further 90 min and then cooled to 25 C. and stirred for a further 16 h. When the reaction had ended, the mixture was saturated with NaOH and extracted with benzene and the solvent was then stripped off on a rotary evaporator. The crude product was purified by distillation (98 C., 18 mm).
	With potassium carbonate; In acetonitrile; for 20h;Heating / reflux;	The N-(3-hydroxypropyl)pyrrolidine used as a starting material was prepared as follows: [00726] A mixture of 3-chloropropanol (66 g), pyrrolidine (50 g), potassium carbonate (145 g) and acetonitrile (1 L) was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was purified by distillation to give the required starting material as an oil (62 g); NMR Spectrum: (CDCl3) 1.6-1.8 (m, 6H), 2.55 (br s, 4H), 2.75 (t, 2H), 3.85 (t, 2H), 5.5 (br s, 1H).

References: [1]Patent: US2003/199491,2003,A1 .
[2]Patent: US2003/212055,2003,A1 .
[3]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6728 - 6737.
[4]Journal of the American Chemical Society,1948,vol. 70,p. 3862.
[5]Pharmazie,1959,vol. 14,p. 201,202.
[6]Tetrahedron Letters,1994,vol. 35,p. 1715 - 1718.
[7]Australian Journal of Chemistry,2007,vol. 60,p. 236 - 242.
[8]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 129.
[9]Patent: WO2007/4735,2007,A1 .Location in patent: Page/Page column 9-10.
[10]Patent: US2003/225111,2003,A1 .Location in patent: Page 41.
[11]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2172 - 2175.
[12]Patent: US2009/264400,2009,A1 .Location in patent: Page/Page column 62.
[13]Patent: US6806274,2004,B1 .Location in patent: Page/Page column 70.

2
[ 19748-66-4 ]
[ 1871-76-7 ]
[ 127158-39-8 ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

3
[ 19748-66-4 ]
[ 7037-44-7 ]
cyclopentyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

4
[ 19748-66-4 ]
[ 49802-71-3 ]
cyclohexyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

5
[ 19748-66-4 ]
[ 874512-36-4 ]
cyclopent-2-enyl-[2]thienyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 2855,2857.

6
[ 19748-66-4 ]
[ 853919-58-1 ]
cyclohex-2-enyl-[2]thienyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 2855,2857.

7
[ 19748-66-4 ]
[ 24168-51-2 ]
fluorene-9-carboxylic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of Organic Chemistry,1950,vol. 15,p. 1013,1015.

8
[ 19748-66-4 ]
[ 91767-44-1 ]
4-isopropoxy-2,6-dimethyl-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Patent: US2719851,1949, .

9
[ 19748-66-4 ]
[ 91767-43-0 ]
2,6-dimethyl-4-propoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Patent: US2719851,1949, .

10
[ 19748-66-4 ]
[ 36823-82-2 ]
4-isopropoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Patent: US2605266,1949, .

11
[ 19748-66-4 ]
[ 40782-58-9 ]
4-propoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Patent: US2605266,1949, .

12
[ 19748-66-4 ]
[ 73331-32-5 ]
2-cyclopentyl-valeric acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

13
[ 19748-66-4 ]
[ 857827-17-9 ]
2-cyclopent-2-enyl-valeric acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

14
[ 19748-66-4 ]
2-cyclopent-2-enyl-hexanoyl chloride [ No CAS ]
2-cyclopent-2-enyl-hexanoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

15
[ 19748-66-4 ]
[ 73331-33-6 ]
cyclopent-2-enyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

16
[ 19748-66-4 ]
[ 872290-82-9 ]
cyclohex-2-enyl-cyclopent-2-enyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

17
[ 19748-66-4 ]
cyclohex-2-enyl-phenyl-acetyl chloride [ No CAS ]
cyclohex-2-enyl-phenyl-acetic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

18
[ 19748-66-4 ]
[ 4521-61-3 ]
[ 101867-45-2 ]

References: [1]Farmaco, Edizione Scientifica,1958,vol. 13,p. 64,72, 73.

19
[ 19748-66-4 ]
[ 10263-19-1 ]
[ 102021-80-7 ]

References: [1]Bollettino Chimico Farmaceutico,1959,vol. 98,p. 646,652.

20
[ 19748-66-4 ]
[ 18780-68-2 ]
[ 118952-80-0 ]

References: [1]Farmaco, Edizione Scientifica,1959,vol. 14,p. 801,806, 807.

21
[ 19748-66-4 ]
[ 33863-86-4 ]
4-butoxy-benzoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of Pharmacy and Pharmacology,1954,vol. 6,p. 119,120, 121.

22
[ 19748-66-4 ]
[ 39743-20-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In benzene; at 0℃; for 4h;Heating; Reflux;	Stage 2. Thionyl chloride (1.5 eq.) was added to a solution of 3-(pyrrolidin-1-yl)propan-1-ol (2 g, 1 eq.) in benzene (5 ml/mmol) at 0 C. The reaction mixture was then heated under reflux for 4 h. The solvent was removed completely and the solid formed was employed further without further purification.

References: [1]Tetrahedron,2007,vol. 63,p. 12903 - 12911.
[2]Journal of the American Chemical Society,1957,vol. 79,p. 5667,5670.
[3]Journal of the American Chemical Society,1954,vol. 76,p. 5099,5100.
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2172 - 2175.
[5]Patent: US2009/264400,2009,A1 .Location in patent: Page/Page column 62.

23
[ 19748-66-4 ]
[ 32633-91-3 ]
[ 47357-40-4 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 3537 - 3541.

24
[ 19748-66-4 ]
[ 94231-78-4 ]
[ 99004-32-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1964,vol. 673,p. 102 - 112.

25
[ 19748-66-4 ]
[ 5860-49-1 ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 4829 - 4831.
[2]Journal of Organic Chemistry,2010,vol. 75,p. 3916 - 3919.
[3]Journal of the American Chemical Society,1960,vol. 82,p. 5148 - 5155.
[4]Tetrahedron Letters,1994,vol. 35,p. 1715 - 1718.

26
[ 123-75-1 ]
[ 504-63-2 ]
[ 19748-66-4 ]
[ 1012-29-9 ]

References: [1]Journal of Organometallic Chemistry,1989,vol. 373,p. 343 - 352.

27
[ 24299-77-2 ]
[ 19748-66-4 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 3164 - 3170.

28
[ 84032-39-3 ]
[ 19748-66-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,1982,vol. 47,p. 2150 - 2156.

29
1-(3-Oxo-propyl)-3,4-dihydro-2H-pyrrolium; chloride [ No CAS ]
[ 19748-66-4 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 3164 - 3170.

30
[ 19748-66-4 ]
[ 125599-27-1 ]
4-(3,4-Dimethoxy-phenyl)-2,6-dimethyl-1-(3-phenyl-propyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-(3-pyrrolidin-1-yl-propyl) ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 818 - 828.

Yield	Reaction Conditions	Operation in experiment
		B. Similarly prepared by use of the appropriate secondary amines and the appropriate omega-haloalcohols are the following N,N-disubstituted aminoalcohols: ...3-(4-morpholinyl)propanol; 3-(1-piperidinyl)propanol; 3-(1-pyrrolidinyl)propanol; 3-(N,N-di-isopropylamino)propanol; ...

32
[ 19748-66-4 ]
2-cyclopentyl-hexanoyl chloride [ No CAS ]
2-cyclopentyl-hexanoic acid-(3-pyrrolidino-propyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3862.

33
[ 5860-49-1 ]
[ 19748-66-4 ]

References: [1]Australian Journal of Chemistry,1999,vol. 52,p. 1131 - 1138.

34
[ 19748-66-4 ]
[ 145091-91-4 ]
5-phenyl-3-(3-pyrrolidin-1-yl-propoxy)-1<i>H</i>-pyrazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 78 - 93.

35
[ 123-75-1 ]
[ 627-18-9 ]
[ 19748-66-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In tetrahydrofuran; at 0 - 20℃; for 15h;	Potassium carbonate (269 g) and pyrrolidine (200 mL) were added in that order to a THF solution (500 mL) of 3-bromopropanol (200 g) at 0°C. The reaction liquid was stirred at room temperature for 15 hours, then ethyl acetate (500 mL) was added to it, and further stirred at room temperature for 1 hour. The obtained reaction liquid was filtered through Celite, and the solid on the Celite was washed with ethyl acetate. The wash liquid and the filtrate were concentrated under reduced pressure, and ethyl acetate (500 mL) was added to the resulting residue, then stirred for 1 hour and filtered through Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified through distillation (boiling point: 62°C, 1 mmHg) to obtain (3-hydroxypropyl)pyrrolidine (156 g, yield 95 percent). 1HNMR (400 MHz, CDCl3, delta ppm): 1.69-1.78 (6H, m), 2.53-2.59 (4H, m), 2.73 (2H, t, J=5.6 Hz), 3.81 1 (2H, t, J=5.4 Hz), 5.58 (1H, brs)
86.3%		To a solution of pyrrolidine (1.5 g, 19.5 mmol) in toluene (10 rnL) was added 3- bromopropanol (5.4 g, 39.0 mmol) and and the reaction mixture heated at 8O0C for 5.5 hrs. After cooling to RT, the toluene was evaporated at reduced pressure and the residue partitioned between DCM (25 mL) and aqueous K2CO3 (25 mL). The organic layer was collected and the aqueous phase extracted with DCM (4 x 25 mL). The combined organic layers were evaporated at reduced pressure to provide the title compound (1.2 g, 86.3 percent) as brown oil.1H NMR (500 MHz, MeOD) delta ppm 3.61 (2 H, t, J=6.3 Hz), 2.48 - 2.71 (6 H, m), 1.70 - 1.89 (6 H, m).
70%	With potassium carbonate; In tetrahydrofuran; at 0 - 20℃; for 15h;	Potassium carbonate (1.4 g, 0.94 mol) and pyrrolidine(0.87 mL, 1.8 mol) were added to a stirred solution of 3-bromopropanol (1 g, 0.635 mol) in30 mL of THF at 0 °C, and the resulting mixture was stirred at room temperature for 15 h.The resulting mixture was diluted with ethyl acetate (200 mL) and filtered through celite.The filtrate was concentrated, and the residue was subjected to column chromatography(silica gel), eluting with 50percent methanol in dichloromethane, to yield a yellow oil (0.57 g,70percent). 1HNMR (300 MHz, CDC13) 3.79 (t, J = 5.1 Hz, 2 H), 2.71 (t, J= 5.6 Hz, 2 H), 2.57-2.51 (m, 4 H), 1.75-1.66 (m, 6 H); ?3C NMR (125 MHz, CDC13) 64.18, 56.02, 54.09,29.24, 23.27.

69%	With potassium carbonate; In tetrahydrofuran; at 0 - 20℃;	Preparation of Compound 48,53-(pyrrolidin-1-yl)propan-1-ol[0068] Pyrrolidine (1 .00 ml_, 12.0 mmol) was added to a suspension of potassium carbonate (1 .29 g, 9.35 mmol) and 3-bromopropanol (0.65 ml_, 7.2 mmol) in dry THF (3 mL) at 0 °C. The reaction mixture was then allowed to warm to rt, stirred overnight, diluted with EtOAc, filtered through a silica pad and the filtrate concentrated to afford the title compound (645 mg, 69percent) as a colourless oil.1H NMR (500 MHz, CDCl3) delta 5.54 (br s, 1 H), 3.84 - 3.77 (m, 2H), 2.77 - 2.68 (m, 2H), 2.60 - 2.53 (m, 4H), 1 .80 - 1 .68 (m, 6H). LRMS (ESI+) (M + H)+: 130.12
59%	In toluene; at 20℃; for 48h;	3-Bromopropan-1-ol (27.3mL, 302mmol) was added to a solution of pyrrolidine (47.2g, 655mmol) in toluene (1000mL) and the mixture was stirred at room temperature for 48 hours. The reaction mixture was then filtered and the filtrate was evaporated under reduced pressure. The residue was distilled and the title product was obtained as a colourless liquid at 100°C/7mmHg, (23.1g, 59percent). 1H-NMR(CDCl3, 400MHz) delta: 1.60-1.82(m, 6H), 2.50-2.60(m, 4H), 2.75(m, 2H), 3.80(m, 2H) MS ES+ m/z 130 [MH]+
	With potassium carbonate; In acetonitrile;Heating / reflux;	A suspension of pyrrolidine (8.35 ml), 3-bromo-1-propanol (8.67 ml), and potassium carbonate (17.28 g) in MeCN (100 ml) was heated under reflux overnight. The reaction mixture was filtered and evaporated in vacuo. The residue was partitioned between EtOAc (100 ml) and 1 M HCl (50 ml). The organic layer was separated and extracted with 1 M HCl (2 x 25 ml). The combined acidic extract was adjusted to pH 13 with solid KOH, while cooling in ice/H2O. The resulting clear, slightly yellowish solution was extracted with DCM (5 x 50 ml). The combined organic extract was dried over Na2SO4 and evaporated in vacuo. The crude product was purified by vacuum distillation employing a 5 cm Vigreux column at a pressure of ca. 15 mbar (with an oil-bath temperature of ca. 120 °C). The fraction distilling off at 89-90 °C was collected. The product was obtained as a colorless oil.

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4780 - 4789.
[2]Patent: EP1852423,2007,A1 .Location in patent: Page/Page column 6; 14.
[3]Patent: WO2009/121812,2009,A1 .Location in patent: Page/Page column 72-73.
[4]Journal of Medicinal Chemistry,2017,vol. 60,p. 3275 - 3288.
[5]Patent: WO2018/118852,2018,A1 .Location in patent: Paragraph 0072.
[6]Patent: WO2015/49535,2015,A1 .Location in patent: Paragraph 0068.
[7]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 107 - 113.
[8]Patent: EP1595881,2005,A1 .Location in patent: Page/Page column 50.
[9]Patent: EP1842846,2007,A1 .Location in patent: Page/Page column 39.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

Related Functional Groups of
[ 19748-66-4 ]

Alcohols

A303797 [104-58-5]

3-(Piperidin-1-yl)propan-1-ol

Similarity: 0.86

A182533 [622-93-5]

3-(Diethylamino)propan-1-ol

Similarity: 0.85

A195186 [13330-96-6]

4-(Dimethylamino)butan-1-ol

Similarity: 0.81

A133564 [104641-59-0]

(S)-(+)-1-Methyl-3-pyrrolidinol

Similarity: 0.80

A159501 [30727-14-1]

1-Ethylpyrrolidin-3-ol

Similarity: 0.80

Related Parent Nucleus of
[ 19748-66-4 ]

Pyrrolidines

A133564 [104641-59-0]

(S)-(+)-1-Methyl-3-pyrrolidinol

Similarity: 0.80

A159501 [30727-14-1]

1-Ethylpyrrolidin-3-ol

Similarity: 0.80

A198212 [13220-33-2]

N-Methyl-3-pyrrolidinol

Similarity: 0.80

A202913 [1210934-04-5]

(S)-(1-Methylpyrrolidin-3-yl)methanol

Similarity: 0.80

A273989 [104641-60-3]

(R)-3-Hydroxy-1-methyl-pyrrolidine

Similarity: 0.80

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 19748-66-4

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