Process for resolving mixtures of carbocyclic stereoisomers
AssigneeGlaxo Wellcome Inc.
InventorsBarry Riddle Sickles, Kenneth James Ingold, Christopher John Wallis
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Abstract
A process for the preparation of carbocyclic stereoisomers of formulae (I), (I'), (IIA'), (IIB'), (VA') and (VB'), including enantiomerically pure (IIA'), (I) and (I') utilizing fractional crystallization of salts formed with a chiral base; a reducing agent; a protecting group removing agent or a protecting group providing agent.
Claims5
A process for the manufacture of an enantiomerically pure compound of formula (IIA') ##STR11## wherein P is selected from C.sub.1-6 alkyloxycarbonyl, aryloxycarbonyl, C.sub.2-6 alkenyloxycarbonyl, C.sub.1-6 alkylaryloxycarbonyl and C.sub.3-6 cycloalkyloxycarbonyl;
- comprising the fractional crystallisation from a suitable solvent of a mixture of diastereomeric salts of the compound of formula (IIA') and the compound of formula (IIB') ##STR12## wherein P is as defined above;
- with a base of formula (IV) ##STR13## wherein R, R.sup.1 and R.sup.2 are independently selected from H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, aryl, C.sub.1-6 alkylaryl and C.sub.3-6 cycloalkyl provided that the groups R, R.sup.1 and R.sup.2 are each different.
A process for the manufacture of an enantiomeric mixture of a compound of formula (IIA') and a compound of formula (IIB') ##STR14## wherein P is selected from C.sub.1-6 alkyloxycarbonyl, aryloxycarbonyl, C.sub.2-6 alkenyloxycarbonyl, C.sub.1-6 alkylaryloxycarbonyl and C.sub.3-6 cycloalkyloxycarbonyl;
- comprising the acid or base hydrolysis of an enantiomeric mixture of a compound of formula (VA') and a compound of formula (VB') ##STR15## wherein P is as defined above.
A process for the manufacture of an enantiomeric mixture of a compound of formula (IIA') and a compound of formula (IIB') ##STR16## wherein P is selected from C.sub.1-6 alkyloxycarbonyl, aryloxyearbonyl, C.sub.2-6 alkenyloxycarbonyl, C.sub.1-6 alkylaryloxycarbonyl and C.sub.3-6 cycloalkyloxycarbonyl;
- comprising the addition of a protecting group to an enantiomeric mixture of a compound of formula (VA) and a compound of formula (VB) ##STR17## by treatment with an appropriate reagent, and the subsequent acid or base hydrolysis of the product in a single `one-pot` reaction.
Dependencies are inferred from the claim text.