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Synfacts 2010(1): 0012-0012  
DOI: 10.1055/s-0029-1218400
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (R)-Sitagliptin

Contributor(s): Philip Kocienski
D. Steinhuebel*, Y. Sun*, K. Matsumura*, N. Sayo, T. Saito
Merck & Co., Rahway, USA and Takasago International Corporation, Hiratsuka City, Japan
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

Sitagliptin is a selective inhibitor of dipeptidyl peptidase IV (DPP-4). It is the active ­antihyperglycemic ingredient in JANUVIA and JANUMET, both of which are used for the treatment of type 2 diabetes. The route depicted features the catalytic asymmetric hydrogenation of enamines generated in situ from β-keto amides using a simple ammonium salt as the nitrogen source to give unprotected β-amino amides in high yield and excellent enantiomeric excess.