Synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an important intermediate for (3S,4R)-Cisapride

TitleSynthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an important intermediate for (3S,4R)-Cisapride
Publication TypeJournal Article
Year of Publication2008
AuthorsShirode, NM, Likhite, AP, Gumaste, VK, Deshmukh, ARakeeb A
JournalTetrahedron
Volume64
Issue30-31
Pagination7191-7198
Date PublishedJUL
Type of ArticleArticle
ISSN0040-4020
Keywords4-aminopiperidine, azetidin-2-ones, Cisapride, Staudinger reaction, stereoselective synthesis
Abstract

An efficient synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an useful intermediate for the chiral synthesis of important drug molecule Cisapride and its analogs, from enantiopure 4-formylazetidin-2-one is described. Synthesis of trans as well as cis isomers of 4-amino-3-methoxypiperidine from 4-formylazetidin-2-one is also achieved in good yield. (c) 2008 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2008.05.090
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.645
Divison category: 
Organic Chemistry