Resolution of the enantiomers of tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via an imine–enamine tautomerism

Resolution of the enantiomers of the sympathomimetic drug tetrahydrozoline was obtained by chiral HPLC. The isolated enantiomers racemize easily and chiral HPLC experiments allowed the determination of the racemization rate constant. This process occurs via an imine–enamine tautomerism which was stu...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1998-08, Vol.9 (16), p.2939-2945
Main Authors: Caccamese, Salvatore, Principato, Grazia
Format: Article
Language:English
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Summary:Resolution of the enantiomers of the sympathomimetic drug tetrahydrozoline was obtained by chiral HPLC. The isolated enantiomers racemize easily and chiral HPLC experiments allowed the determination of the racemization rate constant. This process occurs via an imine–enamine tautomerism which was studied by UV and 1H NMR spectroscopies.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00300-0