title: The absolute configuration of benproperinium dihydrogen phosphate, an antitussive drug.
abstract: 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.
authors.affiliation: Department of Pharmacy, University of Oslo, Norway.
authors.forename: L
authors.initials: L
authors.lastname: Schjelderup
authors.forename: A J
authors.initials: AJ
authors.lastname: Aasen
mesh_terms: D000996:Antitussive Agents / Q000032:analysis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D010880:Piperidines / Q000032:analysis*; D013237:Stereoisomerism
chemical_list: D000996:Antitussive Agents; D007202:Indicators and Reagents; D010880:Piperidines