Prodn. of 14,17-etheno-1,3,5-oestra:tri:en-16-one derivs. - by reacting 16-acetoxy-14,17-etheno-1,3,5-oestratriene-16-carbo:nitrile derivs. with cyanide and ketone

摘要

Prodn. of 3,17beta-dihydroxy-14alpha,17alpha-etheno-1,3,5(10)- oestratrien-16-one (Ia) or 17beta-hydroxy-3-methoxy-14alpha, 17alpha-etheno-1,3,5(10)-estratrien-16-one (Ib) is effected by reacting 3,16beta, 17beta-triacetoxy-14alpha, 17alpha-etheno-1,3,5(10)-oestratriene-16alpha-carbonitrile (IIa) or 16beta, 17beta-diacetoxy-3-methoxy-14alpha, 17alpha-etheno-1,3,5(10)oestratriene-16alpha-carbonitrile with an alkali metal cyanide and a ketone in MeOH. In the formulae X= Ac or Me; Y= H or Me. (IIa) or (IIb) is pref. reacted with NaCN or KCN and acetone at room temp. USE/ADVANTAGE - (I) are intermediates for 14,17-etheno and 14,17-ethano-oestratriene derivs. with oestrogenic activity (EP430386). The process gives high yields (e.g. 80-83%).