A Scalable Synthesis of an Azabicyclooctanyl Derivative, a Novel DPP-4 Inhibitor
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- 作者：Zhongbo Fei ; Quanbing Wu ; Fei Zhang ; Yudong Cao ; Chuanqin Liu ; Wen-Chung Shieh ; Song Xue ; Joe McKenna ; Kapa Prasad ; Mahavir Prashad ; Daniel Baeschlin ; Kenji Namoto
- 刊名：Journal of Organic Chemistry
- 出版年：2008
- 出版时间：November 21, 2008
- 年：2008
- 卷：73
- 期：22
- 页码：9016-9021
- 全文大小：219K
- 年卷期：v.73,no.22(November 21, 2008)
- ISSN：1520-6904
文摘
A practical synthetic strategy to a chiral azabicycclooctanyl derivative (1), a potent DPP-4 inhibitor, starting from a commercially available nortropine is described. The stereogenic center of 1 was established employing a modified protocol of Ellman’s diastereoselective addition of a benzylic nucleophile to tert-butanesulfinimine. Other key steps include Corey−Chaykovsky reaction, Meinwald rearrangement, and CDMT-promoted amide bond formation involving a sterically hindered amine 2.