114636-30-5

Basic information

• Product Name: (S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE
• Synonyms: (S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE;(S)-1-BENZYL-3-ACETYLAMINO PYRROLIDINE;(S)-N-Benzyl-3-AcetylaminoPyrrolidine;(S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE , EE 99%;(S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE, 98%, EE 99%;N-((S)-1-Benzylpyrrolidin-3-yl)acetamide;(S)-N-(1-Benzylpyrrolidin-3-yl)acetaMide;(S)-(-)-1-Benzyl-3-acetamidopyrrolidine, 98%, ee
• CAS NO: 114636-30-5
• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.29
• Mol File: 114636-30-5.mol

Chemical Properties

• Melting Point: 44-46°C
• Boiling Point: 387.3 °C at 760 mmHg
• Flash Point: 188 °C
• Appearance: white or cream-colored solid
• Density: 1.1 g/cm³
• Vapor Pressure: 3.33E-06mmHg at 25°C
• Refractive Index: 1.566
• BRN: 6479772
• CAS DataBase Reference: (S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE(114636-30-5)
• EPA Substance Registry System: (S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE(114636-30-5)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 114636-30-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1-Benzyl-3-acetamidopyrrolidine is utilized as an intermediate in the synthesis of various pharmaceuticals, playing a crucial role in the development of drugs for a range of medical applications. Its versatility in chemical reactions allows for the creation of compounds with potential therapeutic benefits.
Used in the Synthesis of Analgesics:
In the pharmaceutical industry, (S)-(-)-1-benzyl-3-acetamidopyrrolidine is employed as a key intermediate for the production of analgesics, which are essential for managing pain and providing relief to patients suffering from various conditions.
Used in the Synthesis of Anticonvulsants:
Additionally, this compound is used in the synthesis of anticonvulsant drugs, which are vital for treating epilepsy and other seizure disorders. Its unique structure contributes to the development of effective medications that can help control seizures and improve the quality of life for affected individuals.
Used in Organic Compounds Synthesis:
Beyond its pharmaceutical applications, (S)-(-)-1-benzyl-3-acetamidopyrrolidine also serves as an intermediate in the synthesis of various organic compounds, showcasing its broad utility in the field of chemistry and contributing to the discovery of new and potentially beneficial chemical entities.

InChI:InChI=1/C13H18N2O/c1-11(16)14-13-7-8-15(10-13)9-12-5-3-2-4-6-12/h2-6,13H,7-10H2,1H3,(H,14,16)/t13-/m0/s1

Synthetic route

acetic anhydride (108-24-7) + (3S)-3-azido-1-(phenylmethyl)pyrrolidine (114636-29-2) → (R)-N-(1-benzylpyrrolidine-3-yl)acetamide (114636-33-8) + (S)-(-)-1-benzyl-3-acetylaminopyrrolidine (114636-30-5)

Conditions	Yield
With pyridine; hydrogen; triethylamine 1.) methanol, 4 atm, room temperature, 4 h, 2.) room temperature, 16 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

acetic anhydride (108-24-7) + (3S)-1-benzyl-3-pyrrolidinamine (114715-38-7) → (S)-(-)-1-benzyl-3-acetylaminopyrrolidine (114636-30-5)

Conditions	Yield
With pyridine Yield given;

(S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine (131852-53-4) → (S)-(-)-1-benzyl-3-acetylaminopyrrolidine (114636-30-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: CF3CO2H / CH2Cl2 2: pyridine View Scheme

(R)-N-benzyl-3-hydroxypyrrolidine (101385-90-4, 101930-07-8, 101979-03-7, 775-15-5) → (S)-(-)-1-benzyl-3-acetylaminopyrrolidine (114636-30-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / triethylamine / CH2Cl2 / 1.) 0 deg C, 20 min, 2.) room temperature, 1.5 h 2: 87 percent / tetra-n-butylammonium azide / acetonitrile / 1 h / 65 °C 3: 1.) hydrogen, 2.) pyridine, triethylamine / 1.) methanol, 4 atm, room temperature, 4 h, 2.) room temperature, 16 h View Scheme

(R)-3-methanesulfonyloxy-1-(phenylmethyl)-pyrrolidine (114715-35-4) → (S)-(-)-1-benzyl-3-acetylaminopyrrolidine (114636-30-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / tetra-n-butylammonium azide / acetonitrile / 1 h / 65 °C 2: 1.) hydrogen, 2.) pyridine, triethylamine / 1.) methanol, 4 atm, room temperature, 4 h, 2.) room temperature, 16 h View Scheme

Upstream product

• 108-24-7 acetic anhydride 
• 114636-29-2 (3S)-3-azido-1-(phenylmethyl)pyrrolidine 
• 114715-38-7 (3S)-1-benzyl-3-pyrrolidinamine 
• 131852-53-4 (S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 114715-35-4 (R)-3-methanesulfonyloxy-1-(phenylmethyl)-pyrrolidine 

Relevant articles and documents

An efficient conversion of chiral α-amino acids to enantiomerically pure 3-amino cyclic amines

Enantiomerically pure 3-amino cyclic amines such as 3-amino pyrrolidine, 3-amino piperidine, and 2,3,4,5,6,7-hexahydro-1H-azepine have been synthesized in high yields from the optically active natural α-amino acids such as L-aspartic acid, L-glutamic acid, L-2-aminoadipic acid, and their enantiomers.

Asymmetric Synthesis and Properties of the Enantiomers of the Antibacterial Agent 7-(3-Aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic Acid Hydrochloride

Compound 1 is a potent member of the quinoloecarboxylic acid class of antibacterial agents and is currently undergoing clinical evaluation.We have developed efficient asymmetric syntheses of the enantiomers of this agent.The S-(+) enantiomer 1a is 1-2 log2 dilutions more active than the R-(-) enantiomer 1b against aerobic bacteria and 1-2 or more log2 dilutions more active against anaerobic bacteria in vitro.The enantiomer 1a shows significantly better in vivo activity in a Pseudomonas aeruginosa mouse protection model compared to racemic 1.Coupled with the improved solubility profile of 1a relative to racemic material, these features may be of practical significance from a clinical standpoint.