(R)-1-Benzyl-3-pyrrolidinecarbonitrile

Base Information

• Chemical Name: (R)-1-Benzyl-3-pyrrolidinecarbonitrile
• CAS No.: 157528-56-8
• Molecular Formula: C12H14N2
• Molecular Weight: 186.257
• Hs Code.: 2933998090
• European Community (EC) Number: 679-537-3
• DSSTox Substance ID: DTXSID80363948
• Nikkaji Number: J1.387.830G
• Mol file: 157528-56-8.mol

Synonyms:(R)-1-Benzyl-3-pyrrolidinecarbonitrile;157528-56-8;(3R)-1-benzylpyrrolidine-3-carbonitrile;3-Pyrrolidinecarbonitrile, 1-(phenylmethyl)-, (3R)-;(R)-1-Benzyl-3-cyanopyrrolidine;(R)-1-BENZYL-PYRROLIDINE-3-CARBONITRILE;SCHEMBL607249;DTXSID80363948;(3R)-3-Cyano-1-benzylpyrrolidine;MFCD09951967;AKOS006283522;AKOS015839147;AS-68748;B3299;(3R)-1-Benzylpyrrolidine-3alpha-carbonitrile;(R)-1-BENZYLPYRROLIDINE-3-CARBONITRILE;(3R)-1-(phenylmethyl)-3-pyrrolidinecarbonitrile;J-009419

Chemical Property of (R)-1-Benzyl-3-pyrrolidinecarbonitrile

Chemical Property:

• Vapor Pressure: 0.0005mmHg at 25°C
• Refractive Index: 1.5340-1.5380
• Boiling Point: 313.3°C at 760 mmHg
• Flash Point: 132.8°C
• PSA: 27.03000
• Density: 1.08g/cm3
• LogP: 1.96998
• Storage Temp.: 0-10°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.115698455
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

98% ^*data from raw suppliers

(R)-1-Benzylpyrrolidine-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1C#N)CC2=CC=CC=C2
• Isomeric SMILES: C1CN(C[C@@H]1C#N)CC2=CC=CC=C2

Technology Process of (R)-1-Benzyl-3-pyrrolidinecarbonitrile

There total 8 articles about (R)-1-Benzyl-3-pyrrolidinecarbonitrile 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: 91.0%

tetra-n-butylammonium cyanide (10442-39-4) + (S)-methanesulfonic acid 1-benzylpyrrolidin-3-yl ester (118354-71-5) → (R)-1-benzylpyrrolidine-3-carbonitrile (157528-56-8)

Guidance literature:

In acetonitrile; at 65 ℃; for 6h;

DOI:10.1016/0957-4166(94)80138-X

Reference yield: 71.0%

sodium cyanide (143-33-9,25596-52-5) + (S)-methanesulfonic acid 1-benzylpyrrolidin-3-yl ester (118354-71-5) → (R)-1-benzylpyrrolidine-3-carbonitrile (157528-56-8)

Guidance literature:

With cyanure de tetrabutylammonium; In acetonitrile; for 48h; Heating / reflux;

Reference yield:

(R)-2-Dibenzylamino-succinic acid dibenzyl ester → (R)-1-benzylpyrrolidine-3-carbonitrile (157528-56-8)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 14 h, 2.) room temp., 1 h

2: 1.) Et₃N, 2.) H₂ / 2.) 20percent Pd(OH)2/C / 1.) THF, -3 deg C, 1 h, 2.) EtOH, 20 min, 1010 mbar

3: Bu₄NCN / dimethylsulfoxide / 60 h / 60 - 65 °C

With lithium aluminium tetrahydride; hydrogen; tetra-n-butylammonium cyanide; triethylamine; palladium dihydroxide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1055/s-1998-2185

upstream raw materials:

tetra-n-butylammonium cyanide

(S)-methanesulfonic acid 1-benzylpyrrolidin-3-yl ester

sodium cyanide

(R)-2-Dibenzylamino-butane-1,4-diol

Downstream raw materials:

(R)-1-Benzyl-pyrrolidine-3-carboxylic acid; hydrochloride

(R)-C-(1-benzyl-pyrrolidin-3-yl)-methylamine

(R)-1-Benzyl-pyrrolidine-3-carboxylic acid amide

1-cyclopropyl-7-fluoro-9-methyl-8-{3-[1-(methylpiperidin-4-ylamino)cyclopropyl]pyrrolidin-1-yl}-4-oxo-4H-quinolizine-3-carboxylic acid