Stereochemistry of the asymmetric reduction of (1′s)-1,3-dimethyl-4(1′-phenylethylimino)piperidine
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The stereochemistry of the asymmetric reduction of the imine obtained from 1,3-dimethylpiperidin-4-one and (S)-α-phenylethylamine has been studied. It is shown that hydride reduction of imine 1 by sodium borohydride in methanol is asymmetric and gives the cis and trans diastereomeric pair 1,3-dimethyl-4-(α-phenyl-ethylamino) piperidine in the ratio 3:1. Using sodium in isopropanol gives only one trans diastereomeric pair.1H NMR has been used to identify the stereochemical structure and diastereomer excess of the cis and trans isomers of 1,3-dimethyl-4-(α-phenylethylamino)piperidine which had been separated by column chromatography.
KeywordsSodium Methanol Chromatography Organic Chemistry Hydride
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