Diepoxy-androstanes and a process for the preparation thereof

C - Chemistry – Metallurgy – 07 – J

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C07J 1/00 (2006.01) C07J 11/00 (2006.01) C07J 13/00 (2006.01) C07J 31/00 (2006.01) C07J 41/00 (2006.01) C07J 71/00 (2006.01)

Patent

CA 1069497

Abstract of the Disclosure The invention relates to a new compound 5.alpha., 17.beta.-diacetoxy-6.beta.-chloro- 2.alpha.,3.alpha.;16.alpha.,17.alpha.-diepoxy-androstane and to a process for the preparation thereof. The new compound of the invention is a valuable intermediate product in the synthesis of new steroid compounds having curare-like activity. The new com- pound 5.alpha.,17.beta.-diacetoxy-6.beta.-chloro-2.alpha.,3.alpha.;16.alpha.,17.alpha.-diepoxy-androstane is prepared according to the invention by reacting 5.alpha.,17.beta.-dihydroxy-17-oxo-androst-2-ene with an organic sulfonic acid chloride, preferably with methanesulfonic acid chloride and then reacting the obtained 5.alpha.-hydroxy-6.beta.-chloro-17-oxo-androst-2- ene, optionally in the presence of an acid catalyst, with an enol acetate of an aliphatic ketone having 3 to 5 carbon atoms, converting the obtained 5.alpha., 17.beta.-diacetoxy-6.beta.-chloro-androsta-2,16-diene into the corresponding diepoxide by treating it with an organic peracid and finally isolating the desired product from the reaction mixture.

256930

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