合成路线:2) The methylation of 3-methoxy-19-norpregna-1,3,5(10),16-tetraene-20-one (IV) with LiNH2 and methyl iodide in liquid NH3 gives 3-methoxy-17alpha-methyl-19-norpregna-1,3,5(10)-triene-20-one (V),which is reduced with Li in ethanol - NH3 affording the 2,5(10)-diene compound (VI).The hydrolysis of (VI) with acetic acid in acetone - water yields 17alpha-methyl-19-nor-5(10)-pregnene-20-ol-3-one (VII),which is oxidized with CrO3 and H2SO4 in acetone giving 17alpha-methyl-19-nor-5(10)-pregnene-3,20-dione (VIII).Finally this compound is treated with Br2 and MeOH in pyridine.
参考文献标题:
文献作者:Warnant,J.; Farcilli,A.
参考来源:DE 2107835; FR 2077877; GB 1291205; US 3679714; US 3761591; ZA 7100563
合成路线:It can be prepared in two different ways:1) The ketalization of 17alpha-methyl-19-norpregna-4,9-diene-3,20-dione (I) with ethyleneglycol (A),ethyl orthoformate and p-toluenesulfonic acid gives the 3,3-ethylenedioxy ketal (II),which is methylated with potassium tert-butylate and methyl iodide in toluene yielding 3,3-ethylenedioxy-17alpha,21-dimethyl-19-norpregna-5(10),9(11)-diene-20-one (III).Finally this compound is hydrolyzed by treating with an ion-exchange resin (REDEX CF) in refluxing ethanol.
合成路线:2) The methylation of 3-methoxy-19-norpregna-1,3,5(10),16-tetraene-20-one (IV) with LiNH2 and methyl iodide in liquid NH3 gives 3-methoxy-17alpha-methyl-19-norpregna-1,3,5(10)-triene-20-one (V),which is reduced with Li in ethanol - NH3 affording the 2,5(10)-diene compound (VI).The hydrolysis of (VI) with acetic acid in acetone - water yields 17alpha-methyl-19-nor-5(10)-pregnene-20-ol-3-one (VII),which is oxidized with CrO3 and H2SO4 in acetone giving 17alpha-methyl-19-nor-5(10)-pregnene-3,20-dione (VIII).Finally this compound is treated with Br2 and MeOH in pyridine.
参考文献标题:Promegestone
文献作者:Castar,J.; Roberts,P.J.
参考来源:Drugs Fut 1978,3(6),469
产品链接: CAS No. 34184-77-5››