Enantioselective preparation of quinoline derivative

Details Enantioselective preparation of quinoline derivative Enantioselective preparation of quinoline derivative

C - Chemistry, Metallurgy

07

D

C07D 215/26 (2006.01) C07D 251/26 (2006.01)

Patent

CA 2566388

A process for preparing 8-substituted oxy-5-((R)-2-halo-l-hydroxy-ethyl)-(1 H)- quinolin-2-ones or acceptable solvates thereof. The process involves reacting a 5-(.alpha.-haloacetyl)-8-substituted oxy-(1H)-quinolin-2-one with a reducing agent in the presence of a chiral agent and a base to form a 8-(substituted oxy)-5-((R)-2-halo-l-hydroxy-ethyl)-(1H)-quinolin-2-one, said chiral agent having a formula (I) or (II), wherein M, L, X, R1, R2 and R3 have the meanings as indicated in the specification.

La présente invention concerne un procédé permettant de préparer des oxy-5-((<I>R</I>)-2-halo-l-hydroxy-éthyl)-(1H)-quinolin-2-ones substitués à la position 8 ou des solvates acceptables de ceux-ci. Le procédé susmentionné consiste à faire réagir un 5-(.alpha.-haloacétyl)-8-substitué oxy-(1H)-quinolin-2-one avec un agent réducteur en présence d'un agent chiral et d'une base afin de former un 8-(substitué oxy)-5-((<I>R</I>)-2-halo-l-hydroxy-éthyl)-(1H)-quinolin-2-one; lequel agent chiral étant représenté par la formule (I) ou par la formule (II), dans ces formules, M, L, X, R1, R2 et R3 sont tels que définis dans la description.

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