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
• Article Data: 2

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

General Description

(S)-(-)-1-Benzyl-3-acetamidopyrrolidine is a chemical compound with a molecular formula of C14H18N2O. It is a chiral compound, meaning it has an asymmetrical carbon atom, and its enantiomer is (R)-(+)-1-benzyl-3-acetamidopyrrolidine. (S)-(-)-1-BENZYL-3-ACETAMIDOPYRROLIDINE is used as an intermediate in the synthesis of pharmaceuticals and organic compounds. It can be used in the production of drugs for various medical purposes, including analgesics and anticonvulsants. Its unique structure and properties make it a valuable building block for the creation of new and potentially beneficial chemical compounds.

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

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