摘要 |
1,226,356. 18 - Methyl - 19 - nor - 17α- hydroxy - progesterone and its derivatives. SCHERING A.G. 2 April, 1968 [5 May, 1967], No. 15769/68. Heading C2U. [Also in Division C7] The novel 18 - methyl - 19 - nor - 17α - hydroxy - progesterone, the corresponding 4,6 - diene and their 3 - enol - 17α - diesters and 17α- monoesters are prepared by reducing by the Birch method or electrolytically an 18 - methyl- 19 - nor - #<SP>1,3,5(10)</SP> - pregnatriene - 3,17α- diol - 20 - one 3 - alkyl ether 20 - ketal and hydrolysing the product (the corresponding #<SP>2,5(10)</SP> - diene) to give 18 - methyl - 19 - nor- 17α - hydroxy - progesterone and, if desired, converting this to the other products by standard procedures. 20,20 - Ethylenedioxy - 18 - methyl - 19 - nor- #<SP>1,3,5(10)</SP> - pregnatriene - 3,17α - diol 3 - methyl ether is prepared by oxidizing 3 - methoxy - 18- methyl - #<SP>1</SP>'<SP>3</SP>'<SP>5(10)</SP> - estratrien - 17# - ol to the 17- one, converting this to 17α - ethynyl - 18 - methyl- #<SP>1</SP>'<SP>3,5(10)</SP> - estratrien - 3,17# - diol 3 - methyl ether, dehydrating this to 17 - ethynyl - 18 - methyl- #<SP>1'3'5(10)'16</SP> - estratetraen - 3 - ol 3 - methyl ether, hydrating this in the presence of a mercury salt to give 18 - methyl - 19 - nor - #<SP>1,3,5(10),16</SP> - pregnatetraen - 3 - ol - 20 - one 3 - methyl ether, epoxidizing this to give 16α,17α - oxido - 18 - methyl- 19 - nor - #<SP>1</SP>'<SP>3</SP>'<SP>5(10)</SP> - pregnatrien - 3 - ol - 20 - one 3 - methyl ether, converting this via the 16, 17- bromohydrin into 18 - methyl - 19 - nor - #<SP>1,3,5(10)</SP>- pregnatriene - 3,17α - diol - 20 - one 3 - methyl ether and ketalizing this. |