Schjelderup L, Harbitz O, Groth P, Aasen A J
Department of Chemistry, Agricultural University of Norway, Oslo.
Acta Chem Scand B. 1987 May;41(5):356-61. doi: 10.3891/acta.chem.scand.41b-0356.
The absolute configuration of the more active (-)-enantiomer of the anticholinergic trihexyphenidyl hydrochloride has been established as (R) by syntheses of (S)-(+)-procyclidine hydrochloride, whose absolute configuration has been established previously, and (S)-(+)-trihexyphenidyl hydrochloride from the same chiral building block, viz. (S)-(-)-cyclohexyl-3-hydroxy-3-phenylpropanoic acid. Both enantiomers of this chiral synthon were prepared by optical resolution of the corresponding racemate, employing (R)- and (S)-1-phenylethylamine, respectively, as resolving agents.
