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Syntheses of (S)-(+)-trihexyphenidyl Hydrochloride and (S)-(+)-procyclidine Hydrochloride, Two Anticholinergics, Using (S)-(-)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic Acid as Chiral Synthon

L Schjelderup, O Harbitz, P Groth, A J Aasen

Acta Chem Scand B. 1987 May;41(5):356-61.

PMID: 3673449

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1508765-A Procyclidine hydrochloride Procyclidine hydrochloride 1508-76-5 Price
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