Procedure for obtaining the enantiomers of cyzolirtine

C - Chemistry – Metallurgy – 07 – D

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C07D 231/12 (2006.01)

Patent

CA 2299447

The procedure comprises (a) the enantioselective reduction of a pro-chiral ketone (III) by using a reducing and agent and chiral catalyst, both boron derivatives, in an anhydrous solvent or mixture of anhydrous solvents to form an enantiomer of an alcohol (II), and (b), the alkylation of (II), in phase transfer conditions, with optionally prior isolation and purification thereof, with 2-chloro-N,N--dimethylethylamine, to form an enantiomer of (I). Cyzolirtine exhibits analgesic properties.

L'invention concerne un procédé qui consiste à (a) réduire, de manière énantiosélective, une cétone pro-chirale (III) à l'aide d'un agent réducteur et d'un catalyseur chiral dérivés de bore, dans un solvant ou dans un mélange de solvants anhydres pour former un énantiomère d'alcool (II). En outre, ce procédé consiste à (b) assurer l'alkylation de (II) dans des conditions de transfert de phase, éventuellement après avoir isolé et purifié celui-ci, avec du 2-chlore-N, N-diméthyléthylamine, pour former un énantiomère de (I). La cis-olirtine possède des propriétés analgésiques.

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