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. © 2008 Singh et al; licensee Beilstein-Institut.
Singh, S. K., Manne, N., & Pal, M. (2008). Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors. Beilstein Journal of Organic Chemistry, 4. https://doi.org/10.3762/bjoc.4.20