GB805585A - Steroid compounds - Google Patents

Abstract

The invention comprises 5a -halo-steroid compounds of the general formul <FORM:0805585/IV (b)/1> and <FORM:0805585/IV (b)/2> wherein X represents chlorine or bromine, and a process for the preparation of a compound of formula 1 by the acid hydrolysis of a compound of the general formula <FORM:0805585/IV (b)/3> wherein X has the above significance and R represents a group convertible to hydroxy by hydrolysis such as an ether or acyloxy group, which may be prepared by the process described and claimed in Specification 805,584, and a process for the preparation of a compound of formula 2 by the selective oxidation of the 3b -hydroxy group in a compound of formula 1, e.g. by means of a chromium trioxide-pyridine complex. Suitable acids for the hydrolysis step are hydrochloric, sulphuric and p-toluenesulphonic in dilute concentration. The invention also includes a process for the preparation of 3,20 - diketo - 17a - hydroxy - D 4 - pregnene by treating a compound of formula 2 above with an inorganic base, preferably under anhydrous conditions, using a reaction solvent such as methanol, ethanol, hexane, benzene, toluene, xylene, petroleum ether, ether, dioxane or tetrahydrofuran. The inorganic base may be an alkali or alkaline earth metal hydroxide, carbonate or bicarbonate such as sodium or potassium hydroxide. In the examples, the following compounds are prepared : 5a -chloro-3b ,17a - dihydroxy - 20 - keto - pregnane, 5a - chloro - 3,20 - diketo - 17a - hydroxy - pregnane and 3,20-diketo-17a -hydroxy- D 4-pregnene.