GB805583A - Steroid compounds and methods for preparing them - Google Patents

Abstract

The invention comprises cyclopentanophenanthrene compounds of the general formul <FORM:0805583/IV (b)/1> and <FORM:0805583/IV (b)/2> wherein R represents a group convertible to a hydroxy group by hydrolysis, and X represents chlorine or bromine, and the preparation thereof by brominating, e.g., with bromine, a 3-R-5-(bromo or chloro)-bisnorcholanal compound, wherein R has the above significance to produce a compound of the first general formula, and, when required, dehydrobrominating the 3-R-5-(bromo or chloro)-20-bromo-bisnorcholanal to form a compound of the second general formula. A compound of the second general formula is also obtained by reacting a 3-R-5 (bromo or chloro)-bisnorcholanal with bromine in the presence of a weak organic base, and preferably in the presence of an extraneously added bromination catalyst. The dehydrobromination step may be carried out with an organic base or with a solution of a metallic halide, e.g. lithium chloride, magnesium chloride, beryllium chloride and aluminium chloride, or hydrogen bromide in an amide solvent such as an N,N-dialkylacylamide particularly of the formula <FORM:0805583/IV (b)/3> in which R1,R11 and R111 are alkyl groups containing from 1 to 6 carbon atoms. Suitable organic bases for the dehydrobromination step are collidine, pyridine, lutidine and diethylaniline. Suitable weak organic bases are N,N - dialkylacylamides, particularly of the above general formula. Bromination catalysts mentioned are hydrogen bromide, sulphuric acid and organic sulphonic acids such as p-toluene sulphonic acid. In the examples the following compounds are prepared: 3b -acetoxy-5a - chloro - 20 - bromo - bisnorcholanal, and 3b - acetoxy - 5a - chloro - 17(20) - bisnorcholenal. Specifications 805,584 and 805,585 are referred to.