Process for producing optically active oxoheptenoic acid ester

Details Process for producing optically active oxoheptenoic acid ester Process for producing optically active oxoheptenoic acid ester

C - Chemistry, Metallurgy

07

D

C07D 215/14 (2006.01)

Patent

CA 2485580

A novel process for producing an optically active (E)-7-[2-cyclopropyl-4- (4fluorophenyl) quinolin-3-yl]-5-hydroxy-3-oxohept-6-enoic acid ester of formula (III) which is important as an intermediate for synthesizing medicines, comprises reacting 1,3-bis(trimethylsilyloxy)-1-alkoxybuta-1,3-diene of formula (I) with (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-prop-2-en-1-al of formula (II) in the presence of an optically active binaphthol-titanium complex obtained from 1,1'-bi-2-naphthol with titanium tetraisopropoxide, a metal salt and an amine, and then subjecting the reaction product to desilylation. (see formula I)(see formula II)(see formula III)

Cette invention concerne un procédé d'obtention d'un ester d'acide (E)-7-[2-cyclopropyl-4-(4-fluorophényl) quinolin-3-yl]-5-hydroxy-3-oxohept-6-énoïque représenté par la formule (II) et constituant un intermédiaire important pour des médicaments. Ce procédé consiste à faire réagir un 1,3-bis (triméthylsilyloxy)-1-alkoxybuta-1, 3-diène représenté par la formule (I) avec (E)-3-[2-cyclopropyl-4(4-fluorophényl)quinolin-3-yl] prop-2-en-3-al, qui est représenté par la formule (II), en présence d'un complexe de binaphtol-titane optiquement actif obtenu à partir de 1,1'-bi-2-naphtol et de tétraisopropoxyde de titane, et d'un sel de métal et d'une amine, puis en soumettant le produit de réaction à une désilylation. (I) + (II) (III)

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