A Novel Transformation of Primary Amines to N-Monoalkylhydroxylamines

Hidetoshi Tokuyama; Takeshi Kuboyama; Akiko Amano; Tohru Yamashita; Tohru Fukuyama

doi:10.1055/s-2000-6428

Synthesis 2000; 2000(9): 1299-1304
DOI: 10.1055/s-2000-6428

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Novel Transformation of Primary Amines to N-Monoalkylhydroxylamines

Hidetoshi Tokuyama^* , Takeshi Kuboyama, Akiko Amano, Tohru Yamashita, Tohru Fukuyama

^*Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, The Japan Science and Technology Corporation (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax + 81(3)58 02 86 94; E-mail: fukuyama@mol.f.u-tokyo.ac.jp

Abstract

PDF Download All articles of this category

A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.

amine - hydroxylamine - oxidation - cyanomethylation - nitrone

PDF (71 kb)