Collect. Czech. Chem. Commun. 1998, 63, 557-576

Synthesis of Steroid O-(ω-Hydroxyalkyl)oximes by Reduction of Corresponding O-(ω-Carboxyalkyl)oxime Derivatives

Tereza Slavíková, Vladimír Pouzar and Ivan Černý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic


Steroid O-(ω-hydroxyalkyl)oximes with varying alkyl chain length were prepared from the corresponding carboxylic acids using the reduction of mixed anhydrides with sodium borohydride. An unexpected reaction course was observed with O-(2-carboxyethyl)oximes of 3-oxo-4-ene steroids, where a 4,5-dihydroisoxazol-3(2H)-one derivative was formed as a side product.

Keywords: Steroids; O-Alkyl oximes; E/Z Isomers; 4,5-Dihydroisoxazol-3(2H)-ones.