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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-34
classificationIPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-34
filingDate 1992-02-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1993-12-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_dafc3ad83772f806309a1c90a4c280e9
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c306d9df339421e3b9016b772feaf358
publicationDate 1993-12-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-5274117-A
titleOfInvention Process for the enantioselective synthesis of intermediates used in the preparation of physostigmine
abstract A process for the stereoselective synthesis of [R]- and [S]-2,3-dihydro-1,3-dimethyl-2-oxo-1H-indole-3-acetonitriles comprises reacting racemic and 5-alkoxy-substituted (+/-)-1,3-dimethyloxindoles with a halogenated acetonitrile in the presence of a substituted N-benzyl cinchoninium, quinidinium, cinchonidinium, or quininium catalyst. The resulting alkylated oxindoles can be converted to primary amines by catalytic reduction in the presence of hydrogen gas. One of the primary amines, such as enantiomers of 3-(2-aminoethyl)-1,3-dihydro-1,3-dimethyl-5-methoxy-2H-indol-2-one, can be enriched by contact with a chiral tartaric acid in an amount sufficient to preferentially precipitate a salt of the chiral acid and one of the enantiomers. The product can be used in the synthesis of stereospecific forms of physostigmine and related compounds having pharmaceutical activity.
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priorityDate 1990-01-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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