Novel method for isomerising the 10-methyl radical of...

C - Chemistry – Metallurgy – 07 – H

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C07H 17/08 (2006.01) C07B 55/00 (2006.01)

Patent

CA 2254795

An isomerisation method wherein a compound of formula (IA), wherein X and y together form a 3-oxo radical, or X is a hydrogen atom and Y is either a radical (a), where R2 is OH or O-acyl, or an O-alkyl or NH2 radical; R1 is a hydrogen atom or a methyl radical; Z is hydrogen or an acyl radical; and R is a hydrogen atom, an NH2 radical or a (CH2)nAr, NH(CH2)nAr or N=CH(CH2)nAr radical, in the form of a 10 alpha isomer or a mixture of 10 alpha and 10 beta isomers, is exposed to a basic agent to give the corresponding compound of formula (I) in which the 10-methyl radical is in the beta position.

L'invention a pour objet un procédé d'isomérisation caractérisé en ce que l'on soumet un composé de formule (I A), dans laquelle ou bien X et Y forment ensemble un radical 3-oxo, ou bien X représente un atome d'hydrogène et X représente soit un radical (a), dans lequel R2 représente OH ou O-acyle, soit un radical O-alkyle ou NH2, R1 représente un atome d'hydrogène ou un radical méthyle, Z représente un hydrogène ou un radical acyle, R représente un atome d'hydrogène, un radical NH2 ou un radical (CH2)n Ar, NH(CH2)n Ar ou N=CH(CH2)n Ar, sous forme d'isomère 10.alpha. ou de mélange d'isomères 10.alpha. et 10.beta., à l'action d'un agent basique pour obtenir le composé de formule (I) correspondant dans lequel le radical méthyle en 10 est en position .beta..

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