High-performance liquid chromatographic enantioseparation of bicyclic 1,3-amino alcohols

Antal Péter, Judit Kámán, Ferenc Fülöp, Johan Van Der Eycken, Daniel W. Armstrong

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11 Citations (Scopus)

Abstract

Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of diendo- and diexo-3-aminobicyclo[2.2.1]heptane-2-methanol and diendo- and diexo-3-aminobicyclo[2.2.1]hept-5-ene-2-methanol derivatives. Direct separation was carried out on a naphthylethyl carbamate-derivatized β-cyclodextrin (Cyclobond I 2000 SN) stationary phase, which was used in the polar-organic mode. This allowed the simultaneous separation of stereoisomers of alcohol and ester analogs of the bicyclic 1,3-amino alcohols. Alternatively, the derivatization of amino alcohols on the amino group with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide produced diastereomers which were separable with high resolution (Rs>5-10) on a LiChrospher RP-18 stationary phase. The order of elution of the enantiomers was determined by both direct and indirect methods.

Original languageEnglish
Pages (from-to)79-86
Number of pages8
JournalJournal of Chromatography A
Volume919
Issue number1
DOIs
Publication statusPublished - Jun 1 2001

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Keywords

  • 3-Aminobicyclo[2.2.1]hept- 5-ene-2-methanol
  • 3-Aminobicyclo[2.2.1]heptane-2-methanol
  • Bicyclic 1,3-amino alcohols
  • Enantiomer separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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