Verfahren zur Herstellung von 3-(4'Oxo-cyclohexen-2'-yl)-4-(3'hydroxycyclopentyl)-hexan

摘要

1,230,603. Cyclohexenone derivatives. FARBWERKE HOECHST A.G. 29 July, 1968 [29 July, 1967], No. 36099/68. Heading C2C. A novel compound of Formula I is prepared by reacting 3-(41-oxo-cyclohexyl-4- (31-oxocyclopentyl)-hexane II with 2,2,5,5- tetramethyl - 3,4 - dihydroxy - hexane to give the monoketal III reducing the monoketal to give a mixture of the corresponding epimeric alcohols; treating the latter mixture with dilute mineral acid to remove the ketal group; reacting the resultant 3 - (41 - oxo - cyclohexyl) - 4 - (31 - hydroxycyclopentyl)-hexane with an acylating agent; reacting the resulting 31-acyloxy-cyclopentylderivative with bromine to yield 3-(31-bromo-41- oxo - cyclohexyl) - 4 - (31 - acyloxy - cyclopentyl)- hexane; reacting the bromo compound with a lithium halide to give 3-(41-oxo-cyclohexen-21- yl) - 4 - (31 - acetoxycyclopentyl) - hexane; and saponifying the latter compound. The starting material II may be prepared by reacting 3 - (41 - hydroxy - cyclohexyl) - 4 - (41- oxo-cyclohexyl)-hexane with acetic anhydride to give 3 - (41 - acetoxy - cyclohexyl) - 4 - (41-oxocyclohexyl)-hexane, oxidizing the latter with CrO 3 to give the compound VIII ring closing compound VIII, using acetic anhydride to give 3-(41-acetoxy-cyclohexyl)-4-(31- oxo-cyclopentyl)-hexane ; saponifying the latter to give the 41-hydroxy-cyclohexyl-derivative and oxidizing the latter with chromium trioxide in pyridine. Pharmaceutical compositions comprise a compound I in admixture with a suitable diluent or carrier, and have androgenic, gestagenic, antiinflammatory and anabolic activity.