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Synthesis and stereochemistry of tetrahydro‐4‐aryl‐3‐[(dimethylamino)methyl]‐2 H ‐pyranols as potential analgesics
Author(s) -
Mohacsi Erno,
O'Brien Jay P.,
Blount John F.,
Sepinwall Jerry
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270618
Subject(s) - chemistry , diastereomer , enantiomer , stereochemistry , aryl , organic chemistry , alkyl
Diastereomeric cis ‐ and trans ‐tetrahydro‐4‐aryl‐3‐[(dimethylamino)methyl]‐2 H ‐pyranols derived from 3‐[(dimethylamino)methyl]tetrahydro‐4 H ‐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.