Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity

被引：62

作者：

Chen, Cheng-yi

Frey, Lisa F.

Shultz, Scott

Wallace, Debra J.

Marcantonio, Karen

Payack, Joeseph F.

Vazquez, Enrique

Springfield, Shawn A.

Zhou, George

Liu, Ping

Kieczykowski, Gerard R.

Chen, Alex M.

Phenix, Brian D.

Singh, Utpal

Strine, Jeff

Izzo, Brianne

Krska, Shane W.

机构：

[1] Merck Res Labs, Chem Proc Dev & Commercializat, Ctr Mat Sci & Engn, Dept Proc Res, Rahway, NJ 07065 USA

[2] Merck Res Labs, Chem Proc Dev & Commercializat, Ctr Mat Sci & Engn, Dept Med Chem, Rahway, NJ 07065 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2007年 / 11卷 / 03期

关键词：

D O I：

10.1021/op700026n

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chiral amide 1 ( MK- 0364, taranabant) is a potent, selective, and orally bioavailable cannabinoid-1 receptor ( CB-1R) inverse agonist indicated for the treatment of obesity. An asymmetric synthesis featuring a dynamic kinetic resolution via hydrogenation for the preparation of the bromo alcohol 5 is disclosed. Conversion of the alcohol intermediate to the chiral amide 1 is accomplished in good overall yield.

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页码：616 / 623

页数：8

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