GB483926A - Manufacture of compounds of the cyclopentano-hydrophenanthrene series - Google Patents

Abstract

D 5-Unsaturated 3-epi-oxy-compounds of the cyclopentano p - hydrophenanthrene series are prepared by reducing in neutral medium the keto group of a D 5-3-keto compound of the above series. The mixture of stereoisomeric alcohols so obtained may if desired be separated by the use of digitonine. As reducing agents there may be used hydrogen in the presence of a noble or non-noble metal or metal oxide catalyst such as platinum, platinum oxide, nickel, cobalt or a mixture of metals with or without a carrier, or even aluminium amalgam, the essential feature of the process being that the reduction is carried out in neutral medium. In examples: (1) a small amount of active nickel catalyst is added to a cyclohexane solution of D 5-cholestenone. The mixture is then shaken at room temperature with hydrogen, and the reduction product separated into its constituents by means of digitonine, to give pure epi-cholesterol; (2) active nickel catalyst is added to an alcoholic solution of androstendione, and the mixture hydrogenated and treated with digitonine as in example (1) to give D 5-3-epi-oxy-androstenone-(17); (3) active nickel catalyst is added to an alcoholic solution of D 5-testosterone-propionate and the mixture is hydrogenated and treated with digitonine as in example (1) to give D 5-3-epi-oxy-17-oxy-androstene. Specifications 443,463 and 472,294 are referred to.