Patent GB-1096761-A (GB)
Title: Processes for preparing steroids compounds and the compounds when thus prepared
IPC: C07J61/00
Filed: 1964-12-17
Abstract: Novel 17a -alkyl-17b -hydroxy-13b -alkyl-gon-3-ones having the formula <FORM:1096761/C2/1> wherein X represents H or an acyl group derived from a lower organic carboxylic acid having 1-10 carbon atoms, Y represents an alkyl group having 1-10 carbon atoms, and R3 is an alkyl group having 1-4 carbon atoms are obtained in a process which comprises the steps of (i) condensing a 5-oxo-heptenoic acid alkyl ester (wherein the alkyl group contains 1-10 carbon atoms) with a 1,3-dioxo-2-alkyl-cyclopentane (wherein the alkyl group contains 2-18 carbon atoms) in the presence of an alkaline condensation agent, and effecting cyclization and saponification of the condensation product by reaction with an acid or with acid/base couple so as to form a racemic mixture of the corresponding 1,5-dioxo-4-(2-carboxy ethyl)-7a - alkyl - 5,6,7,7a - tetrahydroindane, (ii) resolving the racemic mixture by reaction with an optically active base into the dextrorotatory and laevorotatory enantiomorphs, and reacting the material dextrorotatory in acetone with a mixed hydride so as to form, by reduction of the keto group at the 1-position, the corresponding 1b  - hydroxy - 5 - oxo - 4 - (21 - carboxyethyl)-7ab -alkyl-5,6,7,7a-tetrahydroindane, (iii) subjecting this product to catalytic hydrogenation so as to form the corresponding 1b -hydroxy-5 oxo - (21 - carboxyethyl) - 7ab  - alkyl - 3aa ,4b , 5,6,7,7a-hexahydroindane, (iv) reacting this material with an acylating agent so as to form the d -lactone of the corresponding 1b -acyloxy-4 - (21 - carboxyethyl) - 5 - hydroxy - 7ab  - alkyl-3aa ,4,7,7a-tetrahydroindane, (v) reacting the d -lactone with a ketal of a 4-oxopentyl magnesium halide, reacting the product with an alkali-metal base, and then subjecting the resulting material to acid hydrolysis, so as to form the corresponding 17b -hydroxy-13b -alkyl-4,5 - seco - gon - 9 - ene - 3,5 - dione, (vi) cyclizing this 4,5-seco-gonene in the presence of an alkali-metal-condensation agent so as to form the corresponding 17b -hydroxy-13b -alkyl-gona-4,9-dien-3-one, (vii) reducing this 17b -hydroxy-gonadiene with an alkali metal or an alkaline earth metal in liquid ammonia in the presence of a proton donor so as to form the corresponding 17b -hydroxy-13b -alkyl-gon-5(10)-en-3-one, (viii) reacting this 17b -hydroxy-gon-3-one with an oxidizing agent so as to form the corresponding gon-3,17-dione, and (ix) reacting this product with an alkali-metal derivative of an unsaturated aliphatic hydrocarbon so as to form the corresponding 17a -unsaturated aliphatic-17b -hydroxy-gon-3-one, reacting this unsaturated aliphatic compound with a reducing agent so as to form the corresponding 17a -alkyl derivative, and (xi) subjecting this material to isomerization so as to form the corresponding 17a  - alkyl - 17b  - hydroxy - 13b - alkyl - gon - 4-en-3-one; or (ix1) reacting the gon-5(10)-ene-3, 17-dione product with an alkyl-alkali metal so as to form the corresponding 17a -alkyl-17b -hydroxy-13b -alkyl-gon-4-en-3-one. Pharmaceutical compositions having anabolic activity and containing compounds of the above formula are administered orally, parenterally or rectally.