40499-83-0

Basic information

• Product Name: 3-Pyrrolidinol
• Synonyms: 3-HYDROXYPYRROLIDINE;3-HYDROXYPYRROLINE;3-PYRROLIDINOL;DL-3-HYDROXYPYRROLIDINE;DL-3-PYRROLIDINOL;Pyrrolidin-3-ol;3-pyrrolidinol (DL);3-PYRROLIDINOL FREE BASE
• CAS NO: 40499-83-0
• Molecular Formula: C₄H₉NO
• Molecular Weight: 87.12
• EINECS: 254-944-5
• Product Categories: Alcohols and Derivatives;Building Blocks;C4 to C10;Chemical Synthesis;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 40499-83-0.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 108-110 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.076 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.91±0.20(Predicted)
• BRN: 102542
• CAS DataBase Reference: 3-Pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyrrolidinol(40499-83-0)
• EPA Substance Registry System: 3-Pyrrolidinol(40499-83-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 40499-83-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H9NO/c6-4-1-2-5-3-4/h4-6H,1-3H2

Synthetic route

1-benzyl-3-pyrrolidinol (775-15-5) → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal at 20℃; under 517.148 Torr; for 120h;	92%
With hydrogen; acetic acid; palladium on activated charcoal In ethanol under 3025.3 Torr; for 72h; Parr hydrogenator;	82.9%

C5H13NO4S*ClH → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 20℃; for 2h; Product distribution / selectivity;	92%

BrH*C4H10BrNO → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 20℃; for 1h; Product distribution / selectivity;	87%

1-trimethylsilanyl-2,5-dihydro-pyrrole (70442-87-4) → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
	65%

(+-)-1-benzyl-pyrrolidin-3-ol → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With ethanol; palladium Hydrogenation;

(+-)-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With barium dihydroxide; water at 110 - 115℃;

(+-)-4-chloro-1,2-epoxy-butane + ammonium carbonate → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With ammonia; water

(3RS)-3-hydroxy-4-methanesulfonyloxybutyronitrile (74889-62-6) → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
aluminum nickel In methanol

(RS)-3-hydroxy-4-(methanesulfonyloxy)butylamine hydrochloride (135969-16-3) → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With sodium carbonate In methanol

pyrrole (109-97-7) + diethyl ether (60-29-7) + acrylonitrile (107-13-1) → pyrrolidin-3-ol (40499-83-0) + 2-(ω-carboxyethyl)pyrrole (408309-29-5)

Conditions	Yield
With hydrogenchloride; potassium hydroxide; N-benzyl-trimethylammonium hydroxide

palladium carbon Pd(C) + 4-chloro-3-hydroxybutyronitrile (105-33-9) → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol; ethanol

4-chloro-3-hydroxybutyronitrile (105-33-9) → pyrrolidin-3-ol (40499-83-0)

Conditions	Yield
Stage #1: 4-chloro-3-hydroxybutyronitrile With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 75 - 85℃; for 8.5h; Stage #2: With sodium carbonate In tetrahydrofuran; water at 10 - 70℃; for 15h;

pyrrolidin-3-ol (40499-83-0) + tert-butyl 4-fluorobenzoate (58656-98-7) → N-<4'-(tert-butoxycarbonyl)phenyl>-3-pyrrolidinol (94930-28-6)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 136℃; for 7h;	100%
With potassium carbonate In dimethyl sulfoxide at 120 - 125℃; for 6.5h;	91%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 7h;	85%

pyrrolidin-3-ol (40499-83-0) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine (103057-44-9)

Conditions	Yield
In dichloromethane	100%
With triethylamine In dichloromethane at 20℃; for 16h;	100%
In isopropyl alcohol at 20℃; for 2h;	100%

pyrrolidin-3-ol (40499-83-0) + ethyl 7-chloro-6-fluoro-4-oxo-1-(1,3-thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate (108118-77-0) → ethyl 6-fluoro-1,4-dihydro-7-(3-hydroxy-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate (475468-74-7)

Conditions	Yield
In acetonitrile at 20℃; for 1.5h;	100%

pyrrolidin-3-ol (40499-83-0) + 4-chloroquinoline (611-35-8) → 1-quinolin-4-yl-pyrrolidin-3-ol

Conditions	Yield
In isopropyl alcohol at 100℃;	100%
Stage #1: pyrrolidin-3-ol; 4-chloroquinoline In isopropyl alcohol at 100℃; Stage #2: With potassium carbonate In dichloromethane; water	100%

3-bromo-5-fluorobenzotrifluoride (130723-13-6) + pyrrolidin-3-ol (40499-83-0) → 1-[3-fluoro-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol (1198181-38-2)

Conditions	Yield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; for 16h; Inert atmosphere;	100%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 90℃; for 16h; Inert atmosphere;	100%

pyrrolidin-3-ol (40499-83-0) + 4-{[3-bromo-5-(trifluoromethyl)phenyl]carbonyl}thiomorpholine (1198181-29-1) → 1-[3-(thiomorpholin-4-ylcarbonyl)-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol (1198181-31-5)

Conditions	Yield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 90℃; for 16h; Inert atmosphere;	100%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 90℃; for 16h; Inert atmosphere;	100%

pyrrolidin-3-ol (40499-83-0) + 3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazole-6-carbaldehyde → 1-((3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazol-6-yl)methyl)pyrrolidin-3-ol

Conditions	Yield
Stage #1: pyrrolidin-3-ol; 3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazole-6-carbaldehyde With acetic acid In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 20℃; for 3h;	100%

pyrrolidin-3-ol (40499-83-0) + 3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazole-5-carbaldehyde → 1-((3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazol-5-yl)methyl)pyrrolidin-3-ol

Conditions	Yield
Stage #1: pyrrolidin-3-ol; 3-((2-chloro-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)amino)benzo[d]isothiazole-5-carbaldehyde With acetic acid In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 20℃; for 3h;	100%

pyrrolidin-3-ol (40499-83-0) + 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazine-1-yl)methyl)quinoline (956907-14-5) → 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)pyrrolidin-3-ol

Conditions	Yield
With triethylamine In isopropyl alcohol at 70℃; for 0.5h; Microwave irradiation;	99%
With potassium carbonate In isopropyl alcohol at 80℃; for 0.333333h; Inert atmosphere; Microwave irradiation;

pyrrolidin-3-ol (40499-83-0) + benzyl chloroformate (501-53-1) → benzyl 3-hydroxypyrrolidine-1-carboxylate (95656-88-5)

Conditions	Yield
With sodium carbonate In diethyl ether; water	98%
With triethylamine In dichloromethane at 20℃; for 12h;	57%
In dichloromethane for 20h;	49%

pyrrolidin-3-ol (40499-83-0) + ethyl 7-chloro-1-(2,4-difluorophenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (157373-29-0) → rac-ethyl 1-(2,4-difluorophenyl)-7-(3-hydroxypyrrolidin-1-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	97.5%

pyrrolidin-3-ol (40499-83-0) + Trimethyl-[2-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-ammonium; iodide → 1-[2-(3-Methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-pyrrolidin-3-ol (176762-42-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane at 20℃; for 3h;	97%

pyrrolidin-3-ol (40499-83-0) + 4-Fluoronitrobenzene (350-46-9) → 1-(4-nitrophenyl)pyrrolidin-3-ol (361346-55-6)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 87℃; for 10h; Heating / reflux;	97%
With N-ethyl-N,N-diisopropylamine In acetonitrile for 14h; Heating;

pyrrolidin-3-ol (40499-83-0) + (E)-3-[2-(4-chloro-6-methyl-pyrimidin-2-yl)-vinyl]-benzonitrile (425424-70-0) → (E)-3-{2-[4-(3-hydroxy-pyrrolidin-1-yl)-6-methyl-pyrimidin-2-yl]-vinyl}-benzonitrile

Conditions	Yield
	96%

pyrrolidin-3-ol (40499-83-0) + 6-[(cyclopropylmethyl)(propyl)amino]-N-(4-(formyl-2-methylphenyl))pyrimidine-4-carboxamide (1114592-20-9) → 6-[(cyclopropylmethyl)(propyl)amino]-N-{4-[(3-hydroxypyrrolidin-1-yl)methyl]-2-methylphenyl}pyrimidine-4-carboxamide (1114591-80-8)

Conditions	Yield
Stage #1: pyrrolidin-3-ol; 6-[(cyclopropylmethyl)(propyl)amino]-N-(4-(formyl-2-methylphenyl))pyrimidine-4-carboxamide In dichloromethane for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane for 18h;	96%

pyrrolidin-3-ol (40499-83-0) + 3-fluoro-6-nitrotoluene (446-33-3) → 1-(3-methyl-4-nitrophenyl)-pyrrolidin-3-ol (361346-63-6)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 12h;	95%

pyrrolidin-3-ol (40499-83-0) + phenyl chloroformate (1885-14-9) → benzyl 3-hydroxypyrrolidine-1-carboxylate (95656-88-5)

Conditions	Yield
	95%

pyrrolidin-3-ol (40499-83-0) + tert-butyl 1-(4-(2-chloro-8-(pyridin-2-yl)-9H-purin-9-yl)phenyl)cyclobutylcarbamate (1439393-21-1) → (1-{4-[2-(3-hydroxy-pyrrolidin-1-yl)-8-pyridin-2-yl-purin-9-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (1439393-44-8)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; Inert atmosphere;	95%

pyrrolidin-3-ol (40499-83-0) + 9-bromo-N-(2,5-di-tert-butylphenyl)-perylene-3,4-dicarboxylic imide (165261-51-8) → C40H38N2O3

Conditions	Yield
Stage #1: 9-bromo-N-(2,5-di-tert-butylphenyl)-perylene-3,4-dicarboxylic imide With potassium phosphate In N,N-dimethyl-formamide; toluene for 0.5h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; Stage #2: pyrrolidin-3-ol In N,N-dimethyl-formamide; toluene at 100℃; Buchwald-Hartwig Coupling; Schlenk technique; Sealed tube;	95%

pyrrolidin-3-ol (40499-83-0) + 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid (114610-03-6) → 1-Ethyl-6-fluoro-7-(3-hydroxy-pyrrolidin-1-yl)-4-oxo-1,4-dihydro-cinnoline-3-carboxylic acid (114610-07-0)

Conditions	Yield
In ethanol; acetonitrile for 0.5h; Heating;	94.9%

pyrrolidin-3-ol (40499-83-0) + phenyl chloroacetate (620-73-5) → benzyl 3-hydroxypyrrolidine-1-carboxylate (95656-88-5)

Conditions	Yield
With sodium hydroxide In diethyl ether for 3h;	94%

pyrrolidin-3-ol (40499-83-0) + 1H-benzotriazol-1-yl 2,2-diphenyl-1,3-benzodioxole-5-carboxylate (150192-19-1) → (2,2-diphenyl-benzo[1,3]dioxole-5-yl)-(3-hydroxy-pyrrolidin-1-yl)-methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h;	94%

pyrrolidin-3-ol (40499-83-0) + 6-acetyl-4-chloro-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-indazol-7-yl trifluoromethanesulfonate → 1-(4-chloro-7-(3-hydroxypyrrolidin-1-yl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-indazol-6-yl)ethanone

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 20 - 50℃; for 2.25h;	94%

pyrrolidin-3-ol (40499-83-0) + di-tert-butyl dicarbonate (24424-99-5) + citric acid (77-92-9) → N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine (103057-44-9)

Conditions	Yield
With triethylamine In dichloromethane	93%

pyrrolidin-3-ol (40499-83-0) + N2-{2-[1,3-dihydro-2H-isoindol-2-yl(methyl)amino]-2-oxoethyl}-N2-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-N1-(2-bromoethyl)glycinamide (1190893-61-8) → N2-{2-[1,3-dihydro-2H-isoindol-2-yl(methyl)amino]-2-oxoethyl}-N2-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-N1-[2-(3-hydroxypyrrolidin-1-yl)ethyl]glycinamide (1190893-63-0)

Conditions	Yield
	93%

pyrrolidin-3-ol (40499-83-0) + 2,4-Dichlorobenzenesulfonyl chloride (16271-33-3) → (±)-1-((2,4-dichlorophenyl)sulfonyl)pyrrolidin-3-ol

Conditions	Yield
With sodium carbonate In dichloromethane; water at 0 - 23℃;	93%

pyrrolidin-3-ol (40499-83-0) + ethyl 1-imidazolecarboxylate (19213-72-0) → ethyl 3-hydroxypyrrolidine-1-carboxylate (93591-91-4)

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 15h; Reflux;	92%

pyrrolidin-3-ol (40499-83-0) + 2-bromo-1,4-bis-(trifluoromethyl)-benzene (7617-93-8) → 1-[2,5-bis(trifluoromethyl)phenyl]pyrrolidin-3-ol (1198180-97-0)

Conditions	Yield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 16h; Inert atmosphere;	91%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere;	91%

Upstream product

• 70442-87-4 1-trimethylsilanyl-2,5-dihydro-pyrrole 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 51-35-4 4R-4-hydroxyproline 
• 36901-86-7 cis-hydroxy-D-proline 
• 480452-55-9 (R)-3-tert-butyldimethylsilyloxy-pyrrolidine hydrochloride 
• 177948-70-8 (3R)-N(H)-3-(benzyloxy)pyrrolidine 
• 84367-31-7 (R)-γ-chloro-β-hydroxybutyronitrile 
• 74957-62-3 (R)-3-hydroxy-4-(methanesulfonyloxy)butyronitrile 
• 107-21-1 ethylene glycol 
• 30724-02-8 (4R)-4-hydroxyproline 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 109-97-7 pyrrole 
• 60-29-7 diethyl ether 

Downstream Products

• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 216392-34-6 1-[(tert-butoxycarbonyl)-L-(O-benzyl)tyrosyl]-3(R,S)-pyrrolidinol 
• 103057-44-9 N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine 
• 96-42-4 pyrrolidin-3-one 
• 79278-81-2 1-phenethyl-pyrrolidin-3-ol 
• 13220-33-2 1-methyl-3-pyrrolidinol 
• 42729-56-6 N-isopropyl-3-hydroxypyrrolidine 
• 99065-08-4 1-cyclopentylpyrrolidin-3-ol 
• 51045-31-9 1-cyclohexyl-pyrrolidin-3-ol 
• 775-15-5 1-benzyl-3-pyrrolidinol 
• 727742-01-0 1-(4-fluorobenzyl)pyrrolidin-3-ol 
• 769944-57-2 (S)-1,4-di-(t-butoxycarbonyl)-2-(4-((R)-3-hydroxypyrrolidino)phenyl)piperazine 

Relevant articles and documents

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