ChemInform Abstract: Synthesis and Stereochemistry of Tetrahydro-4-aryl-3-((dimethylamino) methyl)-2H-pyranols as Potential Analgesics

Diastereomeric cis- and trans-tetrahydro-4-aryl-3-[(dimethylamino)methyl]-2H-pyranols derived from 3-[(dimethylamino)methyl]tetrahydro-4H-pyran-4-one (5), have been prepared and their configurations were established on the basis of ir data. The biologically more potent trans isomer 3 was resolved into its optical antipodes and the absolute stereochemistry of one of the enantiomers 14, was determined by X-ray crystallography. Some of the compounds showed analgesic activity comparable to codeine.