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Synlett 2001; 2001(Special Issue): 1003-1005
DOI: 10.1055/s-2001-14646
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Convenient Procedure for One-pot Conversion of Azides to N-Monomethylamines

Hirohisa Kato* , Ken Ohmori, Keisuke Suzuki
  • *Department of Chemistry, Tokyo Institute of Technology, and CREST, Japan Science and Technology Corporation (JST), O-okayama, Meguro-ku, Tokyo 152-8551, Japan; E-mail: ksuzuki@chem.titech.ac.jp
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Publication Date:
31 December 2001 (online)

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One-pot conversion of azides to N-monomethylamines is described. Two optional protocols have been developed, which share the first stage, the reaction of an azide with (CH3)3P to generate the corresponding iminophosphorane. This Staudinger intermediate, thus generated, is either methylated with CH3I and hydrolyzed (method A), or treated with (HCHO) n and reduced with NaBH4 (method B), thereby giving the corresponding N-monomethylamine in high yield.

azides - N-monomethylamines - Staudinger reaction - iminophosphorane - aza-Wittig reaction

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