Manufacture of compounds of the aetio-cholenone or aetio-allo-cholenone series

摘要

Compounds of the aetio-cholenone or aetio-allo-cholenone series are obtained by causing halogen to act on a compound of the aetio-cholanone or aetio-allo-cholanone series and treating the halogen compound so produced with an agent that eliminates hydrogen halide, such as a tertiary amine. Amines mentioned for this purpose are pyridine, quinoline and dimethylaniline. Transformations according to the present invention which are mentioned are the conversion of aetio-cholane dione and aetio - allo - cholanone into androstene - diones-(3 : 17). Androstane-ol-(17)-one-(3) and aetio-allo-cholanol-(17)-one-(3) and their esters into androstene-ol-(17-ones-(3) and esters thereof. In examples: (1) bromine is added to a glacial acetic acid solution of androstane-dione, and the product is precipitated with water. The recrystallized bromo-androstane-dione-(3 : 17) is boiled with dry pyridine for 15 hours, whereupon the solution is acidified and the andro-stene-dione extracted with ether; (2) bromine is added to a glacial acetic acid solution of androstane-ol-(17)-one-(3)-acetate obtained as described in Specification 461,335 and the bromo-androstane-ol-(17)-one-(3)-acetate precipitated with water. This product is treated with boiling quinoline and worked up as in example (1) to give androstene-ol-(17)-one-(3)-acetate. The process can also be applied to aetio-cholanol-(17)-one-(3)-acetate.