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Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: a key intermediate for dipeptidyl peptidase IV inhibitors.


ABSTRACT: An alternative and practical synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile was achieved. Reaction of L-proline with chloroacetyl chloride was followed by conversion of the carboxylic acid moiety of the resulting N-acylated product into the carbonitrile via the corresponding amide intermediate. The synthesized pyrrolidine derivative was utilized to prepare DPP-IV inhibitor Vildagliptin.

SUBMITTER: Singh SK 

PROVIDER: S-EPMC2486489 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature

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Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: a key intermediate for dipeptidyl peptidase IV inhibitors.

Singh Santosh Kumar SK   Manne Narendra N   Pal Manojit M  

Beilstein journal of organic chemistry 20080612


An alternative and practical synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile was achieved. Reaction of L-proline with chloroacetyl chloride was followed by conversion of the carboxylic acid moiety of the resulting N-acylated product into the carbonitrile via the corresponding amide intermediate. The synthesized pyrrolidine derivative was utilized to prepare DPP-IV inhibitor Vildagliptin. ...[more]

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