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Synthesis 2000; 2000(9): 1299-1304
DOI: 10.1055/s-2000-6428
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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
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Publication Date:
31 December 2000 (online)

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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