(R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

Base Information

• Chemical Name: (R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
• CAS No.: 565452-98-4
• Molecular Formula: C7H9ClN2O
• Molecular Weight: 172.61216
• DSSTox Substance ID: DTXSID60448343
• Wikidata: Q72516911
• Mol file: 565452-98-4.mol

Synonyms:565452-98-4;(R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile;(2R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile;(2R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile;(R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile;2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2R)-;SCHEMBL3396562;DTXSID60448343;YCWRPKBYQZOLCD-ZCFIWIBFSA-N;AKOS016015839;CS-0165398;Vildagliptin Chloroacetyl Nitrile (R)-Isomer;(R)-1-(2'-Chloroacetyl)pyrrolidine-2-carbonitrile;2-Pyrrolidinecarbonitrile,1-(chloroacetyl)-,(2R)-(9ci);(R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile? (Vildagliptin Impurity pound(c)

Chemical Property of (R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

Chemical Property:

• Boiling Point: 363.1±37.0 °C(Predicted)
• PKA: -4.65±0.40(Predicted)
• PSA: 44.10000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 0.67768
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.0403406
• Heavy Atom Count: 11
• Complexity: 208

Purity/Quality:

99.5% ^*data from raw suppliers

(2R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)CCl)C#N
• Isomeric SMILES: C1C[C@@H](N(C1)C(=O)CCl)C#N
• Uses: (2R)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile, can be used in the synthesis of 1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine, and Vildagliptin (C363780), which are potent, selective, and orally bioavailable dipeptidyl peptidase IV Inhibitor with Antihyperglycemic properties, that might be used for the treatment of type 2 diabetes.

Technology Process of (R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

There total 6 articles about (R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile 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: 90.0%

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide (214398-99-9) → 1-chloroacetyl-2-cyano-(R)-pyrrolidine (565452-98-4)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In N,N-dimethyl-formamide; at 0 ℃; Large scale;

Reference yield: 66.0%

→ 1-chloroacetyl-2-cyano-(R)-pyrrolidine (565452-98-4)

Guidance literature:

Reference yield:

(R)-1-(2-chloroacetyl)pyrrolidine-2-carboxamide → 1-chloroacetyl-2-cyano-(R)-pyrrolidine (565452-98-4)

Guidance literature:

With trifluoroacetic anhydride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jm030091l

upstream raw materials:

(R)-prolinamide

L-proline

L-prolinamide

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide

Downstream raw materials:

(S)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid {2-[(2-cyanopyrrolidin-1-yl)-2-oxoethylamino]-2-methylpropyl}amide

tert-butyl N-[2-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)-2-methylpropyl]carbamate