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

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

PHA - Molecular Pharmaceutical Science

Tohoku University

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Pages (from-to)	22-24
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	65
Issue number	1
DOIs	https://doi.org/10.1248/cpb.c16-00568
Publication status	Published - 2017

Keywords

3,4-epoxy alcohol
Aminolysis
Chemoselectivity
Lewis acid catalysis
Nemonapride
Protecting-group-free

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10.1248/cpb.c16-00568

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title = "Concise, protecting-group-free synthesis of (+)-nemonapride via Eu(OTf)3-catalyzed aminolysis of 3,4-epoxy alcohol",

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.",

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author = "Uesugi, {Shun Ichiro} and Yusuke Sasano and Shogo Matsui and Naoki Kanoh and Yoshiharu Iwabuchi",

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T1 - Concise, protecting-group-free synthesis of (+)-nemonapride via Eu(OTf)3-catalyzed aminolysis of 3,4-epoxy alcohol

AU - Uesugi, Shun Ichiro

AU - Sasano, Yusuke

AU - Matsui, Shogo

AU - Kanoh, Naoki

AU - Iwabuchi, Yoshiharu

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - 3,4-epoxy alcohol

KW - Aminolysis

KW - Chemoselectivity

KW - Lewis acid catalysis

KW - Nemonapride

KW - Protecting-group-free

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SN - 0009-2363

VL - 65

SP - 22

EP - 24

JO - Chemical and Pharmaceutical Bulletin

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IS - 1

ER -

Concise, protecting-group-free synthesis of (+)-nemonapride via Eu(OTf)₃-catalyzed aminolysis of 3,4-epoxy alcohol

Abstract

Keywords

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