A novel transformation of primary amines to N-monoalkylhydroxylamines

H. Tokuyama, T. Kuboyama, A. Amano, T. Yamashita, T. Fukuyama

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)1299-1304
Number of pages6
Issue number9
Publication statusPublished - 2000


  • Amine
  • Cyanomethylation
  • Hydroxylamine
  • Nitrone
  • Oxidation


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