Method for producing heteroaromatic alcohols free of...

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 487/04 (2006.01) C12N 9/20 (2006.01) C12P 17/18 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2280833

The invention relates to a method for producing enantiomer-free alcohols of formula (I), where the substituents represent the following: R1 is a hydrogen or a substituted or unsubstituted C1-C6-alkyl-, C1-C6-alkoxy-, or C1-C6- alkanoyl-; R2 and R3 independently of each other represent hydrogen or a substituted or unsubstituted C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-alkanoyl, C1- C6-alkylthio-, C1-C6-alkyl sulfinyl or C1-C6-alkyl sulfonyl-; and R4 is not equal R5 and independently of each other they represent either hydrogen or a substituted or unsubstituted C1-C6-alkyl-, or together with the hydrogen atoms to which they are bound form a substituted or unsubstituted C3-C6-cyclo alkylidene. The method is characterized in that racemic compounds of the formula (II), in which the substituents R1 to R5 have the meanings given above and R6 is a substituted or unsubstituted aryl-, C1-C20-alkyl-, C3-C20-alkenyl- , C3-C20-alkynyl-, are reacted with a lipase or esterase in the presence of an alcohol of the formula R7OH (III), where R7 is a substituted or unsubstituted C1-C10-alkyl-.

Procédé de production d'alcools exempts d'énantiomères de formule (I) dans laquelle les substituants ont la signification suivante: R?1¿ est hydrogène ou C¿1?-C¿6?-alkyl-, C¿1?-C¿6?-alcoxy-, ou C¿1?-C¿6?-alcanoyl- substitués ou non substitués; R?2¿ et R?3¿ sont indépendamment l'un de l'autre hydrogène ou C¿1?-C¿6?-alkyl-, C¿1?-C¿6?-alcoxy-, C¿1?-C¿6?-alcanoyl-, C¿1?-C¿6?-alkylthio-, C¿1?-C¿6?-alkylsulfinyl- ou C¿1?-C¿6?-alkylsulfonyl- substitués ou non substitués; R?4¿ et R?5¿ ne sont pas identiques et sont indépendamment l'un de l'autre hydrogène ou C¿1?-C¿6?-alkyl- substitué ou non substitué, ou bien R?4¿ et R?5¿ forment ensemble, avec les atomes de carbone auxquels ils sont liés, un C¿3?-C¿6?-cycloalkylidène substitué ou non substitué. Ledit procédé est caractérisé en ce que des mélanges racémiques de formule (II) dans laquelle les substituants R?1¿ à R?5¿ ont la signification susmentionnée et R?6¿ est aryl-, C¿1?-C¿20?-alkyl-, C¿3?-C¿20?-alcényl- ou C¿3?-C¿20?-alcinyl- substitués ou non substitués, sont mis en réaction avec une lipase ou estérase en présence d'un alcool de formule R?7¿OH (III) dans laquelle R?7¿ est C¿1?-C¿10?-alkyl- substitué ou non substitué.

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