GB795103A - Improvements in or relating to steroid compounds and the preparation thereof - Google Patents

Abstract

The invention comprises steroid compounds having the formula: <FORM:0795103/IV (b)/1> wherein R1 represents a b -hydroxyl or keto group, R2 represents hydrogen or a hydroxyl group and esters and ethers thereof containing 1-10 carbon atoms in the added moiety, and R3 represents an hydroxyl group or a halogen atom, and the preparation thereof by treating the corresponding 15-unsubstituted steroid with a non-oxidizing strong acid, e.g. p-toluene sulphonic acid, to produce a D 14(15)-steroid, which product on treatment with an oxidizing agent, e.g. perbenzoic acid, perphthalic acid or sodium chromate, yields a 14a ,15a -oxidosteroid, which product on treatment with hydrogen halide, e.g. HCl or HBr, or with water containing a non-nucleophilic strong acid catalyst, e.g. perchloric acid or trichloracetic acid, yields compounds of the above formula. The 21-substituent may be esters such as the formate, acetate, propionate, trimethylacetate, benzoate, succinate, phthalate and cyclohexanecarboxylate or ethers such as methyl, ethyl and benzyl. Examples disclose the preparation of 11b ,17a ,21-trihydroxy-4,14-pregnadiene - 3,20 - dione - 21 - acetate, 11b ,17a - dihydroxy - 4,14 - pregnadiene - 3,20 - dione, 17a -hydroxy - 4,14 - pregnadiene - 3,11,20 - trione, 17a ,21 - dihydroxy - 4,14 - pregnadiene - 3,11,20-trione, the corresponding 14a ,15a - oxido - 4-pregnene compounds and the corresponding 14a - hydroxy - 15 - bromo -, chloro - or hydroxy - 4 - pregnene compounds. 17a ,21-Dihydroxy - 4,14 - pregnadiene - 3,11,20 - trione-21 - acetate and 17a ,21 - dihydroxy - 14a ,15a -oxido - 4 - pregnene - 3,11,20 - trione - 21 - acetate are also mentioned. Specifications 761,649, 795,101, 795,104 and 795,105 are referred to.