Document Detail


Syntheses of (S)-(+)-trihexyphenidyl hydrochloride and (S)-(+)-procyclidine hydrochloride, two anticholinergics, using (S)-(-)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid as chiral synthon.
MedLine Citation:
PMID:  3673449     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
L Schjelderup; O Harbitz; P Groth; A J Aasen
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry     Volume:  41     ISSN:  0302-4369     ISO Abbreviation:  Acta Chem. Scand., B, Org. Chem. Biochem.     Publication Date:  1987 May 
Date Detail:
Created Date:  1987-12-14     Completed Date:  1987-12-14     Revised Date:  2000-12-18    
Medline Journal Info:
Nlm Unique ID:  0421265     Medline TA:  Acta Chem Scand B     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  356-61     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Agricultural University of Norway, Oslo.
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MeSH Terms
Descriptor/Qualifier:
Circular Dichroism
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Conformation
Optical Rotation
Phenylpropionates*
Procyclidine / chemical synthesis*
Pyrrolidines / chemical synthesis*
Spectrophotometry, Infrared
Stereoisomerism
Trihexyphenidyl / chemical synthesis*
Chemical
Reg. No./Substance:
0/Indicators and Reagents; 0/Phenylpropionates; 0/Pyrrolidines; 144-11-6/Trihexyphenidyl; 77-37-2/Procyclidine; 78620-93-6/3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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