GB759745A - Steroids - Google Patents

Abstract

The invention comprises a diepoxypregnane of the formula <FORM:0759745/IV(a)/1> wherein R1 and R2 represent hydrogen or an acyl radical of a hydrocarbon carboxylic acid containing up to and including eight carbon atoms, and the preparation thereof by treating a 3b , 20-diacyloxy-5a (6a ), 16a (17a )-dioxido-20-pregnene, with bromine at a temperature between -20 DEG and +10 DEG C. to obtain a 3b -acyloxy - 5a (6a ), 16a (17a ) - dioxido - 21 - bromopregnan-20-one, treating the thus-obtained 21-bromo compound with sodium iodide in acetone to obtain a 3b -acyloxy-5a (6a ), 16a (17a )-dioxido-21-iodopregnan-20-one and treating the 21-iodopregnane with an alkali salt of a carboxylic acid containing up to and including eight carbon atoms, to obtain the corresponding 3b ,21-diacyloxy - 5a (6a ), 16a (17a ) - dioxido - pregnane - 20-one and in the case where R1 and R2 are hydrogen, hydrolysing the thus-obtained ester with at least two equivalents of base. The bromination may be effected in dichloromethylene, chloroform, carbon tetrachloride, benzene, toluene or hexane. As alkali metal salt there may be used the sodium or potassium salt of the selected acid, e.g. acetic, propionic, butyric, valeric, isovaleric, hexanoic, heptanoic, octanoic, trimethylacetic, phenylacetic, benzoic, toluic, anisic, gallic, tartaric, citric, maleic, succinic and salicylic acid. Examples describe the production of 3-acetoxy-, 3b -benzoyloxy-, and 3b -propionyloxy-5a (6a ), 16a (17a )-dioxido-21-acetoxypregnan-20-one and the corresponding 21-bromo-compounds; 3b -benzoyloxy-, and 3b -acetoxy-5a (6a ), 16a (17a )-dioxido-21-benzoyloxypregnane-20-one and 3b ,21-dihydroxy-5a (6a ), 16a (17a ) - dioxidopregnan - 20 one. Other 3b ,21 - diacyloxy - 5a (6a ), 16a (17a ) - dioxidopregnan - 20 - ones are mentioned. Specification 759,247 is referred to.