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Synthesis 1996; 1996(5): 580-582
DOI: 10.1055/s-1996-4271
short paper
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A Facile Preparation of Amino(diethoxyphosphoryl)acetic Esters: Transformation of Phosphoranes to Phosphonic Esters

Masahiko Seki* , Kazuo Matsumoto
  • *Lead Optimization Research Laboratory, Tanabe Seiyaku Co. Ltd., 3-16-89, Kashima, Yodogawa-ku, Osaka 532, Japan, Fax +81(6)3002593; E-mail: m-seki@tanabe.co.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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Triethoxyphosphoranes 8, generated in situ by the treatment of oxalylcarbamates 7 with triethyl phosphite, were reacted with bromotrimethylsilane or hydrogen bromide in acetic acid to afford diethyl phosphonates 9 in high yields. These were readily converted into amino(diethoxyphosphoryl)acetic esters 10 by hydrogenation.

Amino(diethoxyphosphoryl)acetates were conveniently prepared via TMS-Br induced reactions with triethoxyphosphoranes