Process for producing enantiomerically enriched guaifenesin
AssigneeArco Chemical Technology, L.P.
InventorsWilfred P. Shum, Harry Mazurek, Jian Chen
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Abstract
A tertiary amine is used to catalize the stereospecific ring-opening of chiral glycidol with o-methoxyphenol to afford high yields of enantiomerically enriched guaifenesin. The optical purity of the product may be even further enhanced by recrystallization.
Claims14
A method for producing enantiomerically enriched guaifenesin comprising reacting o-methoxy phenol with enantiomerically enriched glycidol in the presence of a catalytically effective amount of a tertiary amine to form the enantiomerically enriched guaifenesin.
A method for producing enantiomerically enriched guaifenesin having an e.e. value of at least 85% comprising reacting o-methoxyphenol with enantiomerically enriched glycidol at a molar ratio of from 2:1 to 1:2 in the presence of from 0.5 to 10 moles of a tertiary amine per mole of o-methoxy phenol at a temperature of from 50.degree. to 150.degree. C. to form the enantiomerically enriched guaifenesin.
A method for producing guaifenesin of high optical purity comprising reacting o-methoxy phenol with enantiomerically enriched glycidol in the presence of a tertiary amine to form enantiomerically enriched guaifenesin and recrystallizing the enantiomerically enriched guaifenesin from a solvent to higher optical purity.
Dependencies are inferred from the claim text.