Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)3-Catalyzed Aminolysis of 3,4-Epoxy Alcohol

Shun-ichiro Uesugi; Yusuke Sasano; Shogo Matsui; Naoki Kanoh; Yoshiharu Iwabuchi

doi:10.1248/cpb.c16-00568

Current Topics: Communications to the Editor

Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)₃-Catalyzed Aminolysis of 3,4-Epoxy Alcohol

Shun-ichiro Uesugi, Yusuke Sasano, Shogo Matsui, Naoki Kanoh, Yoshiharu Iwabuchi

Author information

Keywords: chemoselectivity, aminolysis, 3,4-epoxy alcohol, Lewis acid catalysis, protecting-group-free, nemonapride

JOURNAL FREE ACCESS FULL-TEXT HTML
Supplementary material

2017 Volume 65 Issue 1 Pages 22-24

DOI https://doi.org/10.1248/cpb.c16-00568

Details

Abstract

A concise, protecting-group-free synthesis of the antipsychotic agent (+)-nemonapride has been achieved featuring a europium(III) trifluoromethanesulfonate (Eu(OTf)₃)-catalyzed C4 selective aminolysis of a 3,4-epoxy alcohol by benzylamine and an expedient use of the resulting 4-benzylamino-1,3-diol product for constructing the pyrrolidine skeleton.

Graphical Abstract Fullsize Image

Corresponding author

Register with J-STAGE for free!