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Syntheses of s dextro trihexyphenidyl hydrochloride and s levo procyclidine hydrochloride two anticholinergics using s levo 3 cyclohexyl 3 hydroxy 3 phenylpropanoic acid as chiral synthon

Syntheses of s dextro trihexyphenidyl hydrochloride and s levo procyclidine hydrochloride two anticholinergics using s levo 3 cyclohexyl 3 hydroxy 3 phenylpropanoic acid as chiral synthon

Acta Chemica Scandinavica Series B Organic Chemistry & Biochemistry 41(5): 356-361

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.

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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. Acta Chemica Scandinavica. Series B: Organic Chemistry and Biochemistry 41(5): 356-361, 1987

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