4.4 Article

A concise and efficient synthesis of vildagliptin

Journal

TETRAHEDRON LETTERS
Volume 58, Issue 35, Pages 3426-3428

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.07.062

Keywords

Vildagliptin; DPP-4 inhibitors; 3-Amino-1-adamantanol; L-Prolinamide

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An original synthesis of vildagliptin ((S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyllpyrrolidine-2-carbonitrile), a powerful DPP-4 inhibitor, was developed. Vildagliptin was assembled from 3-amino-ladamantanol, glyoxylic acid and L-prolinamide in a 4-step reaction sequence with the isolation of only two intermediates. The procedure is competitive with existing protocols, leading to vildagliptin in 63% overall yield. (C) 2017 Elsevier Ltd. All rights reserved.

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