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Synthesis 1988; 1988(5): 399-401
DOI: 10.1055/s-1988-27591
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Preparation of Amino(diethoxyphosphoryl)acetic Esters. Catalytic Hydrogenation of Diazo Compounds to Amines

Chihiro Shiraki* , Hiromitsu Saito, Keiichi Takahashi, Chikahiro Urakawa, Tadashi Hirata
  • *Tokyo Research Laboratories, Kyowa Hakko Kogyo Co., Ltd. 3-6-6 Asahi-machi, Machida-shi, Tokyo 194, Japan
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20. August 2002 (online)

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tert-Butyl amino(diethoxyphosphoryl)acetate (2a) is prepared on a multigram scale from tert-butyl diethoxyphosphorylacetate (1a) in a facile two-step synthesis. The method involves the formation of diazo derivative 4 and subsequent catalytic hydrogenation. Compound 2a is also synthesized by reduction of the oxime derivative 3. Direct amination of diethoxyphosphorylacetic esters with chloramine gives other types of esters 2b-e in addition to the tert-butyl ester 2a.