申请人:Schering Aktiengesellschaft
公开号:US04923640A1
公开(公告)日:1990-05-08
A process for the production of 17.alpha.-ethinyl-17.beta.-hydroxy-18-methyl-4,15-estradien-3-one is described comprising reacting a 17-enolester of formula II ##STR1## wherein R.sub.1 represents an alkyl radical with 1-3 carbon atoms and R.sub.2 represents an acyl or a trialkylsilyl group with 1-10 carbon atoms under palladium catalysis, with compounds of formula II ##STR2## wherein R.sub.1 represents an alkyl radical with 1-3 carbon atoms, reducing the 17-keto group to the 17-hydroxy group in a manner known in the art, reducing the aromatic A-ring according to Birch, with liquid ammonia, to 3-methoxy-2,5(10),15-estratrien-17.beta.-ol, reoxidizing the 17-hydroxy group to the 17-keto group, ethinylating the 17-keto group and splitting off the 3-enolether to form 17.alpha.-ethinyl-17.beta.-hydroxy-18-methyl-4,15-estradiene-3-one.
本发明提供了一种制备17α-乙炔基-17β-羟基-18-甲基-4,15-雌二烯-3-酮的方法,包括在钯催化下反应式II的17-烯酰酯:##STR1## 其中R.sub.1代表1-3个碳原子的烷基基团,R.sub.2代表1-10个碳原子的酰基或三烷基硅基团,与式II的化合物反应:##STR2## 其中R.sub.1代表1-3个碳原子的烷基基团,将17-酮基还原为17-羟基,然后按照Birch方法,用液氨还原芳香A环,得到3-甲氧基-2,5(10),15-雌三烯-17β-醇,再将17-羟基重新氧化为17-酮基,乙炔化17-酮基并割离3-烯醚,从而形成17α-乙炔基-17β-羟基-18-甲基-4,15-雌二烯-3-酮。