Enantiomeric resolution of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone
AssigneeBend Research, Inc.
InventorsDouglas A. Lorenz, Daniel J. Brose
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Abstract
There is disclosed a method of separating enantiomers of 4-(3',4'-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone comprising contacting the same with a homogeneous or nonhomogeneous liquid mixture of solvent and water, the mixture containing substantially pure and unsupported gamma-cyclodextrin or its derivatives. Also disclosed are methods of further enantiomerically enriching solid mixtures obtained from the enantiomer separation method and further extracting one enantiomer by solvent extraction of the solid mixtures obtained.
Claims19
A method for separation of enantiomers of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone comprising the steps of:
- (a) contacting said enantiomers with a liquid mixture of water and a solvent, said liquid mixture containing a substantially pure and unsupported binding substance selected from .gamma.-cyclodextrin, anionic poly-.gamma.-cyclodextrin (2-hydroxypropyl)-.gamma.-cyclodextrin, .gamma.-cyclodextrin phosphate sodium salt, succinylated-.gamma.-cyclodextrin, octakis (2,3,6-tri-O-acetyl)-.gamma.-cyclodextrin, and carboxymethyl-.gamma.-cyclodextrin, thereby selectively binding one of said enantiomers to said binding substance;
- and
- (b) separating said binding substance from said liquid mixture
- wherein said enantiomers are soluble in said liquid mixture to at least 1.0 mM and said solvent is selected from the group consisting essentially of alkanes, halogenated alkanes, alkenes, alcohols, ketones, nitriles, ethers, esters, and mixtures thereof and is selected so as to render said binding substance substantially insoluble in said liquid mixture.
A chemical complex of enantiomers of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone and a binding substance selected from .gamma.-cyclodextrin, anionic poly-.gamma.-cyclodextrin, (2-hydroxypropyl)-.gamma.-cyclodextrin, .gamma.-cyclodextrin phosphate sodium salt, succinylated-.gamma.-cyclodextrin, octakis (2,3,6-tri-O-acetyl)-.gamma.-cyclodextrin, and carboxymethyl-.gamma.-cyclodextrin.
A method of improving the enantiomeric excess of a solid mixture of enantiomers of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone that has been enriched in one enantiomer comprising contacting said mixture with sufficient solvent to selectively dissolve up to 95 wt % of said mixture wherein said solvent is selected from methanol, ethanol, acetone, hexane, t-butyl methyl ether, diisopropyl ether, and mixtures of acetone and water.
Dependencies are inferred from the claim text.