NEW PROCESS FOR PRODUCING 17-BETHA-HYDROXY-17-ALPHA-METHYL-2-OXA-5-ALPHA-ANDROSTAN-3-ON, AS WELL AS INTERMEDIATE THEREOF

• Main Authors: LANCOS KRISZTINA LANCOS KRISZTINA, FERENCZINE FODOR KATALIN FERENCZINE FODOR KATALIN, SZELES JANOS SZELES JANOS, HORVATH PETER HORVATH PETER, MAHO SANDOR MAHO SANDOR, SANTA CSABA SANTA CSABA, TROMPLER ARPAD TROMPLER ARPAD, TUBA ZOLTAN TUBA ZOLTAN, MESTER TAMAS MESTER TAMAS
• Format: Patent
• Language: English
• Published: 28.03.2001
• Edition: 7

The invention relates to a new process for the synthesis of 17beta-hydroxy-17alpha-methyl-2-oxa-5alpha-androstane-3-one of formula (I). The process according to the invention is as follows: the 17beta-hydroxy-17alpha-ethyl-1,3-seco-2-nor-5alpha-androstane-1,3-diacid of formula (III) is transformed into the ring-closed 17beta-hydroxy-17alpha-methyl-1,3-seco-2-nor-5alpha-androstane-1,3-diacid anhydride of formula (II) in an inert solvent or without solvent with a C2-C3 alkan acid anhydride or a substituted carbodiimide of formula R1-N=C=N-R2- wherein R1 and R2 independently are C1-C6 alkyl group, C1-C6 alkyl group substituted by tertiary or quaternary amino group or 1-3 phenyl group, C5-C6 cycloalkyl group, aryl group substituted by 1-3 methoxy, tertiary amino, nitro, C1-C4 alkyl group or 1-3 halogen atom-and the obtained compound of formula (II) is reduced regioselectively by a complex alkali metal hydride in an inert solvent The new 17beta-hydroxy-17alpha-methyl-1,3-seco-2-nor-5alpha-androstane-1,3-diacid anhydride of formula (II) is also the subject of the invention.