RESOLUTION OF 1-AZABICYCLO[2.2.2]OCTAN-3-AMINE, 2-(DIPHENYLMETHYL)-N-[[2-METHOXY-5-(1-METHYLETHYL)PHENYL]METHYL]

This invention relates to a process for resolving 1-azabicyclo[2.2.2]octan-3 - amine, 2-(diphenylmethyl)-N-[[2-methoxy-5-(1-methylethyl)phenyl]methyl] comprising reacting 1-azabicyclo[2.2.2]octan-3-amine, 2-(diphenylmethyl)-N-[ [2- methoxy-5-(1-methylethyl)phenyl]methyl] with 1R-(-)-10-camphorsulfon...

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Bibliographic Details
Main Authors TICKNER, DEREK L, MELTZ, MORGAN
Format Patent
LanguageEnglish
French
Published 12.02.2002
Edition6
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Summary:This invention relates to a process for resolving 1-azabicyclo[2.2.2]octan-3 - amine, 2-(diphenylmethyl)-N-[[2-methoxy-5-(1-methylethyl)phenyl]methyl] comprising reacting 1-azabicyclo[2.2.2]octan-3-amine, 2-(diphenylmethyl)-N-[ [2- methoxy-5-(1-methylethyl)phenyl]methyl] with 1R-(-)-10-camphorsulfonic acid in solvent capable of dissolving both of the foregoing reagents, and selectivel y dissolving the camphorsulfonic acid salt of the corresponding (2R, 3R) enantiomer relative to the (2S, 3S) enantiomer, to form the camphorsulfonic acid salt of (2S, 3S)-1-azabicyclo[2.2.2]octan-3-amine, 2-(diphenylmethyl)-N - [[2-methoxy-5-(1-methylethyl)phenyl]methyl], and then optionally hydrolyzing such salt to obtain the free base of the (2S, 3S) enantiomer.
Bibliography:Application Number: CA19962227194