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US 3,946,046 AGranted
Resolution of prostaglandin intermediates by means of oxazolidines
AssigneeThe Upjohn Company
InventorRobert C. Kelly
Life of this patent
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Abstract
Process for resolving a racemic mixture of an oxo-type prostaglandin intermediate by (a) converting the oxo compound by reaction with an optically active ephedrine to a mixture of oxazolidine diastereomers, (b) separating at least one oxazolidine diastereomer from said mixture, (c) hydrolyzing said oxazolidine to free the optically active oxo compound, and (d) recovering said optically active oxo compound.
Claims11
A process for resolving a racemic mixture of an oxo compound of the formula ##SPC36##
- and of the mirror image thereof, wherein R.sub.1 and R.sub.2 are alkyl of one to 4 carbon atoms, inclusive, or, when taken together, ##EQU8## wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.8 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or phenyl, with the proviso that not more than one of the R's is phenyl and the total number of carbon atoms is from 2 to 10, inclusive;
- x is zero or one, and .about. indicates attachment of the moiety to the cyclopropane ring in exo or endo configuration, which comprises the steps of
- a. converting the oxo compound by reaction with an optically active ephedrine to a mixture of oxazolidine diastereomers,
- b. separating at least one oxazolidine diastereomer from said mixture,
- c. hydrolyzing said oxazolidine to free the optically active oxo compound, and
- d. recovering said optically active oxo compound.
3 more elements
Dependencies are inferred from the claim text.