114636-31-6

Basic information

• Product Name: (3S)-(-)-3-ACETAMIDOPYRROLIDINE
• Synonyms: S-AAP;(S)-(-)-3-ACETAMIDOPYRROLIDINE;(S)-3-ACETAMIDO-PYRROLIDINE;(S)-N-PYRROLIDIN-3-YL-ACETAMIDE;(3S)-(-)-3-ACETAMIDOPYRROLIDINE;(3S)-(-)-3-ACETAMIDOPYRROLIDINE 98+%;(S)-3-ACETYLAMINO PYRROLIDINE;(S)-3-Acetaminopyrrolidine
• CAS NO: 114636-31-6
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.17
• EINECS: -0
• Product Categories: 3-Aminopyrrolidines;Amides (Chiral);Chiral 3-Aminopyrrolidines;Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 114636-31-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 56-58°C
• Boiling Point: 70-72°C 40mm
• Flash Point: 70-72°C/40mm
• Appearance: Colorless transparent liquid
• Density: 1.04 g/cm³
• Vapor Pressure: 0.000752mmHg at 25°C
• Refractive Index: -48 ° (C=1, EtOH)
• Storage Temp.: Refrigerator
• PKA: 15.94±0.20(Predicted)
• BRN: 4904139
• CAS DataBase Reference: (3S)-(-)-3-ACETAMIDOPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-(-)-3-ACETAMIDOPYRROLIDINE(114636-31-6)
• EPA Substance Registry System: (3S)-(-)-3-ACETAMIDOPYRROLIDINE(114636-31-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 34-36/37/38-22
• Safety Statements: 26-36/37/39-45-36
• RIDADR: 3259
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 114636-31-6(Hazardous Substances Data)

Usage

General Description

(3S)-(-)-3-Acetamidopyrrolidine, also known as (3S)-(-)-3-Acetyl-1-pyrroline, is a chemical compound with the molecular formula C7H12N2O. It is a derivative of pyrrolidine and is commonly used in organic synthesis and as a chiral auxiliary in asymmetric synthesis. (3S)-(-)-3-Acetamidopyrrolidine is a colorless liquid with a characteristic odor and is soluble in organic solvents. It has applications in the pharmaceutical industry, particularly in the synthesis of chiral pharmaceuticals, due to its ability to introduce chirality into organic compounds. Additionally, it has been investigated for its potential antimicrobial and anti-inflammatory properties. Overall, (3S)-(-)-3-Acetamidopyrrolidine is a versatile compound with various applications in chemical and pharmaceutical industries.

InChI:InChI=1/C6H12N2O/c1-5(9)8-6-2-3-7-4-6/h6-7H,2-4H2,1H3,(H,8,9)/t6-/m0/s1

Synthetic route

acetic anhydride (108-24-7) + (3S)-3-azido-1-(phenylmethyl)pyrrolidine (114636-29-2) → N-[(3R)-3-pyrrolidinyl]acetamide (131900-62-4) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1,2-bis(4-bromo-2,6-dimethoxyphenyl)diazene + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N,N’-((3S,3'S)-((-diazene-1,2-diyl)bis(3,5-dimethoxy-4,1-phenylene))bis(pyrrolidine-1,3-diyl))diacetamide

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos In toluene at 100℃; for 18h; Inert atmosphere;	94%

C45H29N5O + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → C51H41N7O2

Conditions	Yield
at 20℃;	92%

C45H29N5O + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → C51H41N7O2

Conditions	Yield
With triethylamine at 20℃;	92%

2-amino-4-formyl-5-trifluoromethyl-benzoic acid ethyl ester + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → ethyl 4-[[(3S)-3-acetamidopyrrolidin-1-yl]methyl]-2-amino-5-(trifluoromethyl)benzoate

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 1h;	92%

7-chloro-2-(4-chlorobenzyl)-5-methylpyrazolo[1,5-a]pyrimidine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-{(3S)-1-[2-(4-chlorobenzyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-yl]pyrrolidin-3-yl}acetamide

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 95℃;	86.4%

(4-benzenesulfonyl-6-chloropyridin-2-yl)-(5-methyl-1H-pyrazol-3-yl)amine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-{(S)-1-[4-benzenesulfonyl-6-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2-yl]pyrrolidin-3-yl}acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 120℃; for 4h;	86%

3,7-dihydro-9,10-difluoro-3-methyl-7-oxo-2H-pyrido<3,2,1-ij><1,3,4>benzoxadiazine-6-carboxylic acid ethyl ester (137435-09-7) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → 9-((S)-3-Acetylamino-pyrrolidin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic acid ethyl ester

Conditions	Yield
With pyridine Heating;	85%

C14H7Cl3N4O2S (896459-67-9) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → (S)-N-(1-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-ylsulfonyl)pyrrolidin-3-yl)acetamide (896459-68-0)

Conditions	Yield
With triethylamine In dichloromethane for 14h;	81%

C13H9BrClN3 + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → C19H20BrN5O

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 100℃; for 3h; Sealed tube;	81%

(S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) + 2-tert-butyl-6-chloro-9H-purine → N-[(S)-1-(2-tert-butyl-9H-purin-6-yl)pyrrolidin-3-yl]acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃; for 16h;	76%

2-[3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,4-triazol-1-yl]benzoyl chloride + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(3S)-1-{2-[3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,4-triazol-1-yl]benzoyl}pyrrolidin-3-yl]acetamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h;	76%

2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (885618-31-5) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → (S)-N-(1-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-methyl)pyrrolidin-3-yl)acetamide

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In chloroform at 20℃; for 16h;	74%

p-benzyloxyphenylbromide (6793-92-6) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(S)-1-(4-benzyloxyphenyl)pyrrolidin-3-yl]acetamide

Conditions	Yield
With potassium phosphate; CVT-2537 In dimethyl sulfoxide at 110℃; for 16h; Inert atmosphere;	71%

N-((3-(3,4-difluorophenyl)-4,5-dihydroisoxazol-5-yl)methyl)propane-2-sulfonamide + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-((3S)-1-(2-fluoro-4-((5S)-5-((1-methylethylsulfonamido)methyl)-4,5-dihydroisoxazol-3-yl)phenyl)pyrrolidin-3-yl)acetamide

Conditions	Yield
With potassium carbonate at 135 - 140℃; Sealed tube; Inert atmosphere;	68%

5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (1312684-94-8) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → 8-[(3S)-3-(acetylamino)pyrrolidin-1-yl]-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide (1312685-07-6)

Conditions	Yield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In tetrahydrofuran at 65℃;	66%

(3R,4S)-4-(4-bromophenyl)-1-(2-fluoro-6-methylbenzyl)-N,N-dimethylpyrrolidin-3-amine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → C26H35FN4O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In 1,4-dioxane at 100℃; under 1034.32 Torr; for 8h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;	64%

4,5-dichloro-3-nitropyridin-2-ylamine (662116-67-8) + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → (S)-N-(1-(2-amino-5-chloro-3-nitropyridin-4-yl)pyrrolidin-3-yl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 45℃; for 18h;	61%

2-{[(2S)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4-[(4-methoxybenzyl)oxy]benzoic acid + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(3S)-1-(2-{[(2S)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4-[(4-methoxybenzyl)oxy]benzoyl)pyrrolidin-3-yl]acetamide

Conditions	Yield
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 20h;	59%

7-chloro-5-methyl-2-{1-[4-(trifluoromethyl)phenyl]ethyl}pyrazolo[1,5-a]pyrimidine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(3S)-1-(5-methyl-2-{1-[4-(trifluoromethyl)phenyl]ethyl}pyrazolo[1,5-a]pyrimidin-7-yl)pyrrolidin-3-yl]acetamide

Conditions	Yield
With triethylamine In acetonitrile at 60℃; Inert atmosphere;	46.1%

N-[1-(5-{2-[(dimethylamino)methyl]phenyl}thiophen-2-yl)ethyl]-6-fluoro-2-methylpyrido[3,4-d]pyrimidin-4-amine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(3S)-1-(4-{[(1S)-1-(5-{2-[(dimethylamino)methyl]phenyl}thiophen-2-yl)ethyl]amino}-2-methylpyrido[3,4-d]pyrimidin-6-yl)pyrrolidin-3-yl]acetamide

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 170℃;	46%

7-chloro-2-[1-(4-chlorophenyl)ethyl]-5-methylpyrazolo[1,5-a]pyrimidine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(3S)-1-{2-[1-(4-chlorophenyl)ethyl]-5-methylpyrazolo[1,5-a]pyrimidin-7-yl}pyrrolidin-3-yl]acetamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃;	43.2%

6-(chloromethyl)-N-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenyl)picolinamide + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → (S)-6-((3-acetamidopyrrolidin-1-yl)methyl)-N-(4-(piperidin-1-yl)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)picolinamide

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 3h;	39%

(S)-2-(2-(2-(1H-pyrazol-1-yl)ethyl)-6-(methoxycarbonyl)-7-methyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-f]quinolin-3-yl)acetic acid + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → methyl (S)-2-(2-(1H-pyrazol-1-yl)ethyl)-3-(2-((S)-3-acetamidopyrrolidin-1-yl)-2-oxoethyl)-7-methyl-3,7,8,9-tetrahydro-6H-imidazo[4,5-f]quinoline-6-carboxylate

Conditions	Yield
With 2-chloro-1,3-dimethylimidazolinium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; 1,2-dichloro-ethane at 20℃; for 20h;	34%

methyl 6-(4-bromo-3-methylphenyl)pyrazine-2-carboxylate + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → methyl 6-[4-[(3S)-3-acetamidopyrrolidin-1-yl]-3-methylphenyl]pyrazine-2-carboxylate

Conditions	Yield
With potassium phosphate; palladium diacetate; ruphos In toluene for 3h; Molecular sieve; Inert atmosphere; Reflux;	33%

(S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) + 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid - difluoroboron complex → 7-((S)-3-Acetylamino-pyrrolidin-1-yl)-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 120℃; for 14h;	31%

2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-methylidenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-((3 S)-1-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxain-7-yl)ethyl)pyrrolidin-3-yl)acetamide

Conditions	Yield
Stage #1: 2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-methylidenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde; (S)-N-(pyrrolidin-3-yl)acetamide In tetrahydrofuran at 20℃; for 10h; Stage #2: With sodium cyanoborohydride In tetrahydrofuran at 20℃; for 2h;	29.1%

2-(2-(3-(bromomethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → (S)-2-(2-(3-((3-Acetamidopyrrolidin-1-yl)methyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 3h;	24%

7-chloro-2-[1-(5-chloropyridin-2-yl)ethyl]-5-methylpyrazolo[1,5-a]pyrimidine + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → N-[(3S)-1-{2-[1-(5-chloropyridin-2-yl)ethyl]-5-methylpyrazolo[1,5-a]pyrimidin-7-yl}pyrrolidin-3-yl]acetamide

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 90℃; for 10h;	15.2%

2-(6-(3-(difluoromethyl)-4-fluorophenyl)-3-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)acetic acid + (S)-N-(pyrrolidin-3-yl)acetamide (114636-31-6) → (S)-N-(1-(2-(6-(3-(difluoromethyl)-4-fluorophenyl)-3-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)acetyl)pyrrolidin-3-yl)acetamide

Conditions	Yield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h;	15%

Upstream product

• 108-24-7 acetic anhydride 
• 114636-29-2 (3S)-3-azido-1-(phenylmethyl)pyrrolidine 

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