GB759743A - Steroids - Google Patents

Abstract

The invention comprises a 3-oxygenated 5a (6a ), 16a (17a )-diepoxypregnan-20-one of the formula <FORM:0759743/IV(a)/1> wherein R represents hydrogen or an acyl radical of a hydrocarbon carboxylic acid containing up to and including eight carbon atoms, and the preparation thereof by mixing a 3b ,20-diacyloxy-5,16,20-pregnatriene with an organic peracid, e.g. perbenzoic, peracetic, performic or monoperphthalic acid at a temperature between -10 DEG and +40 DEG C. to give a 3b ,20-diacyloxy-5a (6a ), 16a (17a ) - diepoxy - 20 - pregnene and hydrolysing the thus-obtained diepoxy-20-pregnene with a strong base to obtain 3b -hydroxy - 5a (6a ), 16a (17a ) - diepoxypregnan-20-one, and treating the latter with an acylating agent such as ketene, isopropenyl acylate, an acid anhydride, an acid chloride or an acid bromide. The hydrolysis may be effected by means of an alkali hydroxide, sodamide, calcium hydroxide, barium hydroxide or sodium carbonate. The acylation may be effected in pyridine, benzene, toluene or ether as solvent. Examples describe the production of 3b -hydroxy - 5a (6a ), 16a (17a ) - diepoxypregnan - 20-one and the corresponding 3b -acetoxy-, 3b -propionyloxy-, 3b -benzoyloxy- and 3b -(b -cyclopentylpropionyloxy)-esters thereof. Specification 759,247 is referred to.