Process for the preparation of an enantiomerically enriched...

C - Chemistry – Metallurgy – 07 – C

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C07C 251/24 (2006.01)

Patent

CA 2506110

Process for the preparation of an enantiomerically enriched Schiff base wherein an amine is contacted with a carbonyl compound wherein the amine and/or the carbonyl compound is a chiral compound, to form a mixture of the enantiomers of the corresponding Schiff base wherein, if the amine is the chiral compound the carbonyl compound is an aromatic aldehyde; if the carbonyl compound is the chiral compound the amine is an aromatic amine and if both the amine and the carbonyl compound are chiral compounds, they in combination may have the same meanings as given above for bath the chiral amine and the chiral carbonyl compound situation, and the mixture of enantiomers of the Schiff base is subjected to preparative chromatography on a stationary phase whereby separation of the enantiomers of the Schiff base is obtained. Preferably chiral Simulated Moving Bed chromatography is used.

L'invention concerne un procédé permettant la préparation d'une base de Schiff énantiomériquement enrichie. Ce procédé consiste à faire entrer en contact une amine avec un composé carbonyle, l'amine et/ou le composé carbonyle étant un composé chiral, afin de former un mélange des énantiomères de la base de Schiff correspondante. Si l'amine constitue le composé chiral, le composé carbonyle est un aldéhyde aromatique, et si le composé carbonyle constitue le composé chiral, l'amine est une amine aromatique. Si l'amine et le composé carbonyle sont tous deux des composé chiraux, ils peuvent conjointement répondre aux deux significations décrites à la fois pour la situation amine chirale et la situation composé carbonyle chiral. L'étape suivante consiste à soumettre le mélange d'énantiomères de la base de Schiff à une chromatographie préparatrice sur une phase stationnaire, de manière à produire une séparation des énantiomères de la base de Schiff. A cette fin on utilisera de préférence une chromatographie chirale sur lit mobile simulé.

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