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Stereochemistry of diastereoisomeric propionyl esters of 4‐(2‐furyl)‐3‐methyl‐1‐phenethyl‐piperidin‐4‐ols and the analgesic ether derived from their acid‐catalysed ethanolysis
Author(s) -
Casy A. F.,
Dewar G. H.,
Pascoe R. A.
Publication year - 1983
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/omr.1270210212
Subject(s) - chemistry , analgesic , derivative (finance) , ether , alkoxy group , stereochemistry , organic chemistry , medicinal chemistry , alkyl , pharmacology , medicine , financial economics , economics
The stereochemistry of diastereoisomeric propionyl esters of 4‐(2‐furyl)‐3‐methyl‐1‐phenethylpiperidin‐4‐ols has been established by 13 C NMR analysis. Both isomers, after acid‐catalysed ethanolysis, are converted to the corresponding 4‐ethoxy derivative of configuration ( t ‐3‐Me, r ‐4‐OEt) that correlates with its analgesic properties.