The absolute configuration of benproperinium dihydrogen phosphate, an antitussive drug.
The (+)- and (-)-enantiomers of benproperinium dihydrogen phosphate, an antitussive drug, have been assigned the R- and S-configurations, respectively, by syntheses of both enantiomers using (S)-2-hydroxypropanoic acid (L-lactic acid) as chiral synthon. The key intermediate, (S)-1-methyl-2-[2-(phenylmethyl)phenoxy]ethyl p-toluenesulfonate, was subjected to an SN2-type reaction with piperidine furnishing (+)-(R)-benproperinium dihydrogen phosphate. (-)-(S)-Benproperinium dihydrogen phosphate was obtained by submitting the same tosylate to two consecutive SN2-type reactions with Br- and piperidine, respectively, acting as nucleophiles.
Schjelderup
L
L
Department of Pharmacy, University of Oslo, Norway.
Aasen
A J
AJ
D000996:Antitussive Agents / Q000032:analysis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D010880:Piperidines / Q000032:analysis*; D013237:Stereoisomerism
D000996:Antitussive Agents; D007202:Indicators and Reagents; D010880:Piperidines