(R)-N-(1-Benzylpyrrolidin-3-yl)acetamide

Base Information

• Chemical Name: (R)-N-(1-Benzylpyrrolidin-3-yl)acetamide
• CAS No.: 114636-33-8
• Molecular Formula: C13H18N2O
• Molecular Weight: 218.299
• European Community (EC) Number: 622-502-4
• DSSTox Substance ID: DTXSID00556133
• Wikidata: Q72442954
• Mol file: 114636-33-8.mol

Synonyms:114636-33-8;(R)-N-(1-Benzylpyrrolidin-3-yl)acetamide;N-[(3R)-1-Benzylpyrrolidin-3-yl]acetamide;Acetamide, N-[(3R)-1-(phenylmethyl)-3-pyrrolidinyl]-;(R)-(+)-BENZYL-3-ACETYLAMINOPYRROLIDINE;(R)-1-Benzyl-3-acetylamino pyrrolidine;SCHEMBL1781392;DTXSID00556133;CMSWETNAAPYFSH-CYBMUJFWSA-N;AKOS016843300;AS-75790;CS-0513973;N-((R)-1-BENZYLPYRROLIDIN-3-YL)ACETAMIDE;(R)-(+)-1-Benzyl-3-acetylaminopyrrolidine, 97%;N-[(3R)-1-(phenylmethyl)-3-pyrrolidinyl]acetamide;BRD-K41610306-001-01-1

Chemical Property of (R)-N-(1-Benzylpyrrolidin-3-yl)acetamide

Chemical Property:

• Vapor Pressure: 3.33E-06mmHg at 25°C
• Refractive Index: n20/D 1.5470(lit.)
• Boiling Point: 387.283 °C at 760 mmHg
• PKA: 15.89±0.20(Predicted)
• Flash Point: 188.022 °C
• PSA: 32.34000
• Density: 1.101 g/cm³
• LogP: 1.72580
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 218.141913202
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

98%min ^*data from raw suppliers

(R)-N-(1-Benzylpyrrolidin-3-yl)acetamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1CCN(C1)CC2=CC=CC=C2
• Isomeric SMILES: CC(=O)N[C@@H]1CCN(C1)CC2=CC=CC=C2

Technology Process of (R)-N-(1-Benzylpyrrolidin-3-yl)acetamide

There total 5 articles about (R)-N-(1-Benzylpyrrolidin-3-yl)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

acetic anhydride (108-24-7) + (R)-1-benzyl-3-aminopyrrolidine (114715-39-8) → (R)-N-(1-benzylpyrrolidine-3-yl)acetamide (114636-33-8,28506-01-6)

Guidance literature:

In dichloromethane; at 20 ℃; for 1.25h; Heating / reflux;

Reference yield:

acetic anhydride (108-24-7) + (3S)-3-azido-1-(phenylmethyl)pyrrolidine (114636-29-2) → (R)-N-(1-benzylpyrrolidine-3-yl)acetamide (114636-33-8,28506-01-6) + (S)-(-)-1-benzyl-3-acetylaminopyrrolidine (114636-30-5,28506-01-6)

Guidance literature:

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

DOI:10.1021/jm00403a017

Reference yield:

(R)-N-benzyl-3-hydroxypyrrolidine (101385-90-4,101930-07-8,101979-03-7,775-15-5) → (R)-N-(1-benzylpyrrolidine-3-yl)acetamide (114636-33-8,28506-01-6)

Guidance literature:

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

With pyridine; hydrogen; tetrabutylammoniun azide; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jm00403a017

upstream raw materials:

acetic anhydride

(S)-N-benzyl-3-hydroxypyrrolidine

(3S)-3-azido-1-(phenylmethyl)pyrrolidine

(R)-N-benzyl-3-hydroxypyrrolidine

Downstream raw materials:

(R)-1-benzyl-N-ethylpyrrolidine-3-amine

(3'R)-7-(3'-aminopyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Refernces

• 1、 -. "JANUS KINASE 1 SELECTIVE INHIBITOR AND PHARMACEUTICAL USE THEREOF". Paragraph 0229-0237. . Retrieved 2018/06/07.
• 2、 Rosen, Terry,Chu, Daniel T. W.,Lico, Isabella M.,Fernandes, Prabhavathi B.,Shen, Linus,et al.. "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". . p. 1586 - 1590. Retrieved 2007/10/02.