952506-23-9Relevant articles and documents
A scalable synthesis of an azabicyclooctanyl derivative, a novel DPP-4 inhibitor
Fei, Zhongbo,Wu, Quanbing,Zhang, Fei,Cao, Yudong,Liu, Chuanqin,Shieh, Wen-Chung,Xue, Song,McKenna, Joe,Prasad, Kapa,Prashad, Mahavir,Baeschlin, Daniel,Namoto, Kenji
experimental part, p. 9016 - 9021 (2009/04/06)
(Chemical Equation Presented) 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.