GB813335A - Improvements in 17-aromatic sulfonate-16-hydroxy steroids - Google Patents

Abstract

The invention comprises 5 - androstene - 3,16,17 - triol - 17 - p - toluenesulphonate, 1,3,5(10) - estratriene - 3,16,17 - triol - 3,17 - di-(p - toluenesulphonate), 3 - methoxy - 1,3,5(10)-estratriene - 16,17 - diol - 17 - p - toluenesulphonate and 3-methoxy-1,3,5(10)-estratriene-16-acetoxy-17-p-toluenesulphonate, and a process for the preparation of 17-aromatic sulphonate - 16 - hydroxy - steroids by reacting an aryl sulphonyl halide with a 17-hydroxy-16-keto-steroid of the general formula: <FORM:0813335/IV (b)/1> wherein ring A represents a ring having no double bond, or one, two or three double bonds, ring B represents a ring having no double bond or one or two double bonds, Y represents hydrogen or a methyl group when C10 carbon is not joined by a double bond to another carbon atom, and X represents a hydroxy, acyloxy or ether group, to form the corresponding 17-aromatic sulphonate-16-keto-steroid and reducing the said sulphonate with an alkali metal aluminium hydride or an alkali metal borohydride. The above process may be modified in that in the case where the 17-hydroxy-16-keto-steroid reactant of the above general formula contains a free hydroxy group at the 3-position, the aromatic sulphonate group present at the 3-position resulting from the reaction with an aryl sulphonyl halide is selectively hydrolysed with dilute sulphuric acid to a hydroxy group prior to the reduction step. The above process may also be extended by acetylating the hydroxy group at the 16-position. The aryl sulphonyl halide may be p-toluene sulphonyl chloride. Suitable reducing agents specified are lithium aluminium hydride and sodium borohydride. In the examples the four compounds referred to as above as forming part of the invention and 3-methoxy-5-androstene - 16,17 - diol - 17 - p - toluenesulphonate are prepared. Specification 813,334 is referred to.