Process for the production of 17.alpha.-acetoxy-1.alpha.,2.alpha.-methylene-4,6-pregnadiene-3,20-dione
AssigneeSchering Corporation
InventorHanfried Arnold
Life of this patent
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Abstract
A multistep process for production of 17.alpha.-acetoxy-1,2-methylene-4,6-pregnadiene-3,20-dione involves ketalization of the 20-keto group of 17.alpha.-hydroxy-1,4,6-pregnatriene-3,20-dione, then methylenation in the 1,2-position with trimethylsulfoxonium iodide, hydrolysis and simultaneous acetylation of the 17.alpha.-hydroxy group.
Claims7
A process for the production of 17.alpha.-acetoxy-1,2-methylene-4,6-pregnadiene-3,20-dione comprising ketalizing the 20-keto group of 17.alpha.-hydroxy-1,4,6-pregnatriene-3,20-dione with ethylene glycol in the presence of a trialkyl formate and a strong acid;
- methylenating the resultant 20-ketal steroid in the 1,2-position by reacting it with trimethylsulfoxonium iodide in a polar aprotic solvent in the presence of a strong base;
- hydrolyzing the resultant product;
- and acetylating the resulting 17.alpha.-hydroxy-1,2-methylene-4,6-pregnadiene-3,20-dione by reacting it with a reactive derivative of acetic acid in the presence of a strong inorganic or organic sulfonic acid.
17.alpha.hydroxy-1,4,6-pregnatriene-3-one-20-ethylene ketal.
Dependencies are inferred from the claim text.