9-alpha-hydroxysteroids, process for their preparation,...

Details 9-alpha-hydroxysteroids, process for their preparation,... 9-alpha-hydroxysteroids, process for their preparation,...

C - Chemistry, Metallurgy

07

J

167/192, 260/7

C07J 1/00 (2006.01) C07J 5/00 (2006.01) C07J 7/00 (2006.01) C07J 13/00 (2006.01) C07J 21/00 (2006.01) C07J 31/00 (2006.01) C07J 33/00 (2006.01) C07J 41/00 (2006.01) C07J 43/00 (2006.01)

Patent

CA 1334844

9.alpha.-Hydroxy steroids are prepared directly from 9.alpha.- hydroxy steroids as starting compounds without any protec- tion of the 9.alpha.-hydroxyl group. A suitable starting compound is 9.alpha.-hydroxyandrost-4-ene-3,17-dione which is readily available from fermentative degradation of sterols. Two preferred preparations are the production of a 9.alpha.-hyd- roxy,17-cyano,17-hydroxy steroid by reacting said starting compound with a cyanohydrin forming agent, for example potassium cyanide, and the other preferred reaction is the production of a 9.alpha.-hydroxy,17-ethynyl,17-hydroxy steroid by reacting said starting compound with a usual ethynylating agent, such as lithium acetylide ethylene diamine complex. The obtained 17-ethynyl compound can be converted to a pregnane compound, particularly a 17.beta.-acetyl or 17.beta.-halo- acetyl steroid with a 9.alpha.- as well as a 17.alpha.-hydroxyl group by hydrating the ethynyl group or the haloethynyl group res- pectively.

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