13220-33-2

Basic information

• Product Name: 1-Methyl-3-pyrrolidinol
• Synonyms: N-Methyl-pyrrolidin-3-ol;1-Methyl-3-hydroxypyrrolidine;NSC 89279;N-Methyl-pyrrolidinyl alcohol;1-Methyl-3-pyrrolidinol,97%;1-Methyl-3-pyrrolidi;3-Hydroxy-1-methylpyrroli...;N-Methyl-3-hydroxy-
• CAS NO: 13220-33-2
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.15
• EINECS: 236-189-3
• Product Categories: Heterocyclic Compounds;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 13220-33-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 50-52 °C1 mm Hg(lit.)
• Flash Point: 159 °F
• Appearance: Colorless or light yellow liquid
• Density: 0.921 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.132mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.95±0.20(Predicted)
• CAS DataBase Reference: 1-Methyl-3-pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-pyrrolidinol(13220-33-2)
• EPA Substance Registry System: 1-Methyl-3-pyrrolidinol(13220-33-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 13220-33-2(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

1-Methyl-3-pyrrolidinol (cas# 13220-33-2) is a compound useful in organic synthesis.

InChI:InChI=1/C5H11NO/c1-6-3-2-5(7)4-6/h5,7H,2-4H2,1H3/p+1/t5-/m0/s1

Synthetic route

1,4-dibromo-2-butanol (19398-47-1) + methylamine (74-89-5) → 1-methyl-3-pyrrolidinol (13220-33-2) + 1,4-bis(methylamino)butan-2-ol (1404453-61-7)

Conditions	Yield
In water at 100℃; for 16h; Inert atmosphere;	A 98% B 0.9 g

1,4-dichlorobutan-2-ol (2419-74-1) + methylamine (74-89-5) → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
In water at 10 - 120℃; under 7500.75 Torr; for 10h; Temperature; Pressure; Autoclave; Sealed tube;	64.8%

4-methylamino-3-hydroxybutyronitrile → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
	56%

CH3 NH2 + 1,4-dibromo-2-butanol (19398-47-1) → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
	25%

ethyl-3-oxo-1-pyrrolidinecarboxylate (14891-10-2) → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
With lithium aluminium tetrahydride

1,4-dibromo-2-butanol (19398-47-1) + methylamine (74-89-5) → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
With ethanol at 125 - 130℃;

1-methyl-2,5-dihydro-pyrrole (554-15-4) → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide Product distribution; var. hydroborating agents, olefin to hydroborating agent ratios, and times; other N-substituted-3-pyrrolines;

1.1-dimethyl-3-oxy-pyrrolidinium chloride → 1-methyl-3-pyrrolidinol (13220-33-2)

ethyl-3-oxo-1-pyrrolidinecarboxylate (14891-10-2) + diethyl ether (60-29-7) + lithium alanate → 1-methyl-3-pyrrolidinol (13220-33-2)

pyrrolidin-3-ol (40499-83-0) + formaldehyd (50-00-0) → 1-methyl-3-pyrrolidinol (13220-33-2)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran

1-methyl-3-pyrrolidinol (13220-33-2) → 1-methyl-1-oxypyrrolidin-3-ol (1404453-62-8)

Conditions	Yield
With dihydrogen peroxide In ethanol for 21h; Inert atmosphere;	100%

1-methyl-3-pyrrolidinol (13220-33-2) + N-hydroxyphthalimide (524-38-9) → 2-(1-methylpyrrolidin-3-yloxy)isoindoline-1,3-dione (160229-79-8)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 6h; Inert atmosphere;	97%

phenylacetic acid (103-82-2) + 1-methyl-3-pyrrolidinol (13220-33-2) → 1-methyl-3-pyrrolidinyl phenylacetate (434332-38-4)

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	91%

1-methyl-3-pyrrolidinol (13220-33-2) + Methyl ferulate (2309-07-1) → (E)-methyl 3-(3-methoxy-4-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 0℃; for 0.5h;	89%

1-methyl-3-pyrrolidinol (13220-33-2) + Z-1,4-dichlorobutene (1476-11-5) → (Z)-1,1'-(but-2-ene-1,4-diyl)bis(3-hydroxy-1-methylpyrrolidinium) chloride

Conditions	Yield
In acetonitrile at 20℃; Inert atmosphere;	88%

1-methyl-3-pyrrolidinol (13220-33-2) + 4-fluoro-2-methoxy-1-nitrobenzene (448-19-1) → 3-(3-methoxy-4-nitro-phenoxy)-1-methyl-pyrrolidine (1001345-84-1)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; toluene at 18 - 60℃; for 18h;	87%
With potassium hydroxide; tetrabutylammomium bromide In water; toluene at 60℃; for 18h;	87%
With sodium hydride In acetonitrile at 80℃;

1-methyl-3-pyrrolidinol (13220-33-2) + N-(4-fluoro-2-methoxy-5-nitrophenyl)-8-(3-fluorophenyl)quinazolin-2-amine → 8-(3-fluorophenyl)-N-(2-methoxy-4-((1-methylpyrrolidin3-yl)oxy)-5-nitrophenyl)quinazolin-2-amine

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: N-(4-fluoro-2-methoxy-5-nitrophenyl)-8-(3-fluorophenyl)quinazolin-2-amine In N,N-dimethyl-formamide at 20℃; for 0.5h;	86.1%

1-methyl-3-pyrrolidinol (13220-33-2) + methanesulfonyl chloride (124-63-0) → 1-methylpyrrolidin-3-yl methanesulfonate (91832-73-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	81%
With triethylamine In benzene for 0.75h; Ambient temperature;
With triethylamine In dichloromethane at -10 - 20℃; for 2.08333h;
With triethylamine In dichloromethane at 20℃; for 1.5h; Cooling with ice; Inert atmosphere;
With sodium hydroxide In dichloromethane at 0℃;	124 g

1-methyl-3-pyrrolidinol (13220-33-2) + C20H15ClF3N3O4 → C25H24ClF3N4O4

Conditions	Yield
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In tetrahydrofuran at 20℃; Cooling with ice;	78.5%

1-methyl-3-pyrrolidinol (13220-33-2) + (R)-(3-((5-bromopyrimidin-2-yl)amino)pyrrolidin-1-yl)(3-fluoro-4-nitrophenyl)methanone → ((R)-3-((5-bromopyrimidin-2-yl)amino)pyrrolidin-1-yl)(3-((1-methylpyrrolidin-3-yl)oxy)-4-nitrophenyl)methanone

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: (R)-(3-((5-bromopyrimidin-2-yl)amino)pyrrolidin-1-yl)(3-fluoro-4-nitrophenyl)methanone In tetrahydrofuran; mineral oil at 0℃; for 1h; Enzymatic reaction;	73%

3-HYDROXYPYRIDINE (109-00-2) + 1-methyl-3-pyrrolidinol (13220-33-2) → 3-(1-methyl-3-pyrrolidinyloxy)-pyridine

Conditions	Yield
Stage #1: With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: 1-methyl-3-pyrrolidinol In tetrahydrofuran at -20℃; for 0.166667h; Stage #3: 3-HYDROXYPYRIDINE In tetrahydrofuran at 20℃; Mitsunobu reaction;	72.9%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran	260 mg (72.9%)

1-methyl-3-pyrrolidinol (13220-33-2) + 2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester (19833-96-6) → 3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine (13118-11-1)

Conditions	Yield
With sodium In n-heptane for 3h;	72%

1-methyl-3-pyrrolidinol (13220-33-2) + 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (427-49-6) → 3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine (13118-11-1)

Conditions	Yield
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In toluene at 20℃; for 0.5h; Stage #2: 1-methyl-3-pyrrolidinol In toluene at 20℃;	71%
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 18℃; Stage #2: 1-methyl-3-pyrrolidinol In N,N-dimethyl-formamide at 18 - 60℃; for 19h; Product distribution / selectivity;
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 18 - 60℃; for 19h; Inert atmosphere;
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 1-methyl-3-pyrrolidinol In N,N-dimethyl-formamide at 60℃;	Ca.580 g

(R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester (64471-47-2) + 1-methyl-3-pyrrolidinol (13220-33-2) → N-methyl-3-pyrrolidinyl (-)-cyclopentylmandelate (873912-87-9)

Conditions	Yield
With sodium In n-heptane for 2h;	70%

1-methyl-3-pyrrolidinol (13220-33-2) + ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate (1007170-16-2) → Ethyl 6-{4-chloro-3-[(1-methylpyrrolidin-3-yl)oxy]phenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate (1007170-22-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; Inert atmosphere;	70%

1-methyl-3-pyrrolidinol (13220-33-2) + 3-nitro-5-(trifluoromethyl)phenol (349-57-5) → 1-methyl-3-(3-nitro-5-(trifluoromethyl)phenoxy)pyrrolidine (1529769-19-4)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 15h; Cooling with ice;	67%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 15h; Cooling with ice;	67%

1-methyl-3-pyrrolidinol (13220-33-2) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 1-methylpyrrolidin-3-yl ester (60499-30-1)

Conditions	Yield
With triethylamine In dichloromethane for 5h;	66%
With potassium hydroxide In tetrahydrofuran at 0 - 25℃; for 16h;	65%
With potassium hydroxide In tetrahydrofuran at 0 - 25℃; for 16h;	44%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	31%
With triethylamine In dichloromethane

1-methyl-3-pyrrolidinol (13220-33-2) + 2-(4-fluorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (295320-15-9) + tributylphosphine (998-40-3) + 1,1'-(Azodicarbonyl)dipiperidin (10465-81-3) → 2-(4-fluorophenyl)-1-[4-(1-methylpyrrolidin-3-yloxy)benzyl]-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (295320-23-9)

Conditions	Yield
In tetrahydrofuran; dichloromethane	56%
In tetrahydrofuran; dichloromethane	56%

1-methyl-3-pyrrolidinol (13220-33-2) + N,N-Dimethylcarbamoyl chloride (79-44-7) → (RS)-1-methyl-3-pyrrolidinyl N,N-dimethylcarbamate

Conditions	Yield
With sodium hydride In toluene Ambient temperature;	52%

1-methyl-3-pyrrolidinol (13220-33-2) + bis(trichloromethyl) carbonate (32315-10-9) + (19Z,22Z)-octacosa-19,22-dien-11-ol → 1-methylpyrrolidin-3-yl (9Z,12Z)-octacosa-19,22-dien-11-yl carbonate

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; (19Z,22Z)-octacosa-19,22-dien-11-ol With pyridine In toluene at 0 - 10℃; for 1.33333h; Stage #2: 1-methyl-3-pyrrolidinol In toluene at 0 - 20℃;	50%

1-methyl-3-pyrrolidinol (13220-33-2) + 5-hydroxy-1-(2-trimethylsilanylethoxymethyl)-1H-indazole-3-carboxylic acid ethyl ester (865886-86-8) → 5-(tetrahydro-2H-pyran-4-yloxy)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-indazole-3-carboxylic acid (869782-61-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 16h; Mitsunobu reaction;	49%

1-methyl-3-pyrrolidinol (13220-33-2) + 4-Fluoronitrobenzene (350-46-9) → 1-methyl-3-(4-nitrophenoxy)pyrrolidine (943751-42-6)

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Stage #2: 4-Fluoronitrobenzene In tetrahydrofuran for 2h;	44%
With sodium hydride In 1-methyl-pyrrolidin-2-one

1-methyl-3-pyrrolidinol (13220-33-2) + 2-amino-N-(4-methoxypyridin-3-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide → 2-amino-N-(4-methoxypyridin-3-yl)-5-((1-methylpyrrolidin-3-yl)oxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Conditions	Yield
Stage #1: 2-amino-N-(4-methoxypyridin-3-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.0833333h; Stage #2: 1-methyl-3-pyrrolidinol With caesium carbonate In acetonitrile at 20℃; for 1h;	44%

1-methyl-3-pyrrolidinol (13220-33-2) + 2-chloro-8-cyclopentyl-1-propyl-1,7-dihydro-purin-6-one (1303954-15-5) → 8-cyclopentyl-2-(1-methylpyrrolidin-3-yl)oxy-1-propyl-7Hpurin-6-one (1303953-67-4)

Conditions	Yield
With sodium hydride In mineral oil for 3h; Inert atmosphere; Reflux;	41%

1-methyl-3-pyrrolidinol (13220-33-2) + 2-cyclopentyl-2-hydroxy-2-phenylacetic-1-[1-14C] acid → 1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenyl-[1-14C]acetate + 1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenyl-[1-14C]acetate

Conditions	Yield
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic-1-[1-14C] acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-methyl-3-pyrrolidinol In N,N-dimethyl-formamide at 20 - 60℃;	A 41% B n/a

1-methyl-3-pyrrolidinol (13220-33-2) + 4-(chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline + diethylazodicarboxylate (1972-28-7) → 4-(4-chloro-2-fluoranilino)-6-methoxy-7-(1-methylpyrrolidin-3-yloxy)quinazoline hydrochloride hydrate

Conditions	Yield
With hydrogenchloride; triphenylphosphine In methanol; dichloromethane; isopropyl alcohol	40%

1-methyl-3-pyrrolidinol (13220-33-2) + 3-[2-[2-(3-hydroxy-phenyl)-acetylamino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester (1154427-47-0) → 3-[2-{2-[3-(1-methyl-pyrrolidin-3-yloxy)-phenyl]-acetylamino}-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester (1154427-56-1)

Conditions	Yield
Stage #1: 1-methyl-3-pyrrolidinol; 3-[2-[2-(3-hydroxy-phenyl)-acetylamino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0(2,6)]dec-4-yl)-ethyl]-benzoic acid tert-butyl ester With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane Stage #2: With water In dichloromethane	34%

Upstream product

• 131237-81-5 3-hydroxy-N-methylsuccinimide 
• 2419-74-1 1,4-dichlorobutan-2-ol 
• 74-89-5 methylamine 
• 19398-47-1 1,4-dibromo-2-butanol 
• 40499-83-0 pyrrolidin-3-ol 
• 50-00-0 formaldehyd 
• 14891-10-2 ethyl-3-oxo-1-pyrrolidinecarboxylate 
• 60-29-7 diethyl ether 
• 554-15-4 1-methyl-2,5-dihydro-pyrrole 

Downstream Products

• 68165-06-0 1-methylpyrrolidin-3-one 
• 22349-82-2 C₁₂H₁₈NO⁽¹⁺⁾*Br^(1-) 
• 1404453-57-1 C₁₂H₁₈NO⁽¹⁺⁾*Cl^(1-) 
• 13118-11-1 3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine 
• 1404453-84-4 cyclopentyl(1-methyl-pyrrolidin-3-yloxycarbonyl)phenylmethyl ester 
• 1404453-66-2 3-benzoyloxy-1,1-dimethylpyrrolidinium bromide 
• 65976-16-1 1-benzyl-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1-methylpyrrolidinium bromide 
• 129784-12-9 (3R,2'S)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide 
• 129784-12-9 (3S,2'R)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide 
• 13220-17-2 3-benzoyloxy-1-methyl-pyrrolidine 
• 1404453-67-3 3-(2-cyclopentylidene-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide 
• 1404453-52-6 1-[3-(benzylmethylamino)-2-hydroxypropyl]-3-hydroxy-1-methylpyrrolidinium bromide 
• 117446-81-8 2-[2-[bis(phenylmethyl)amino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione 
• 117427-78-8 2-[2-(dimethylamino)ethyl]-2,3-dihydro-4-methyl-7-phenylpyrido-[3,2-f]-1,4-oxazepine-5(4H)-thione 

Relevant articles and documents

Preparation method of 1-methyl-3-pyrrolidinol

The invention relates to the technical field of synthesis of medical intermediates, and particularly discloses a preparation method of 1-methyl-3-pyrrolidinol. The preparation method comprises the following steps that S1, a compound I and a compound II are subjected to a ring closing reaction, so a compound III is obtained; and S2, the compound III obtained in the step S1 and a reducing agent IV are subjected to a reduction reaction, so 1-methyl-3-pyrrolidinol is obtained, wherein the compound I, the compound II and the compound III are as shown in the specification; and the reducing agent IV is one or more selected from a group consisting of sodium borohydride, potassium borohydride, boron trifluoride-diethyl ether and boron tribromide-diethyl ether. According to the preparation method, the compound II and the compound I are selected and subjected to the ring closing reaction to obtain the intermediate compound III, and the compound III is solid and is easy to crystallize and purify, so the purification difficulty of the intermediate is reduced, the purity of the intermediate is favorably improved, and the product quality of the 1-methyl-3-pyrrolidinol is further improved.

Carry over of impurities: A detailed exemplification for glycopyrrolate (NVA237)

The original synthesis of glycopyrrolate (NVA237) was revised and shortened into an essentially one-pot process. Without isolating the intermediates, their purification became obsolete, thereby increasing the possibility of the carry over of impurities. For that reason, the actual, potential, and theoretical impurities of the starting materials cyclopentyl mandelic acid and 1-methyl-pyrrolidin-3-ol as well as byproducts which may occur during the synthesis were thoroughly investigated; furthermore, their transformation to possible impurities in the drug substance along the new synthetic route was performed to exclude them as actual impurities in the drug substance with certainty. The question is raised how detailed such investigation-which are fairly manageable for a simple product like glycopyrrolate-need to be.

Process for preparing 3-pyrrolidinols

A novel process is disclosed for the preparation of 3-pyrrolidinol compounds selected from the group having the formula: STR1 wherein: R is selected from hydrogen, loweralkyl, loweralkenyl, cycloalkyl, cycloalkyl-loweralkyl, phenyl-loweralkyl and substituted phenyl-loweralkyl; R1, R2, and R3 are selected from hydrogen, loweralkyl, and loweralkenyl; and the optical isomers thereof. In the process, 4-amino-3-hydroxybutyronitriles are reductively cyclized with Raney nickel to produce the 3-pyrrolidinol compound.