Liquid chromatographic direct resolution of aryl alpha-amino ketones on a residual silanol group-protecting chiral stationary phase based on optically active (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6

Hee Jung Choi; Jong Sung Jin; Myung Ho Hyun

doi:10.1016/j.jchromb.2008.05.047

Liquid chromatographic direct resolution of aryl alpha-amino ketones on a residual silanol group-protecting chiral stationary phase based on optically active (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6

J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Nov 1;875(1):102-7. doi: 10.1016/j.jchromb.2008.05.047.

Authors

Hee Jung Choi¹, Jong Sung Jin, Myung Ho Hyun

Affiliation

¹ Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, South Korea.

PMID: 18562257
DOI: 10.1016/j.jchromb.2008.05.047

Abstract

A residual silanol group-protecting chiral stationary phase (CSP) based on optically active (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 was successfully applied to the resolution of racemic cathinone and it analogue aryl alpha-amino ketones. The separation factors (alpha) and the resolutions (Rs) for 12 analytes were in the ranges of 2.85-16.12 and 6.49-19.64, respectively. The chromatographic resolution behaviors were investigated as a function of the content and type of organic and acidic modifiers and the ammonium acetate concentration in aqueous mobile phase. The practical usefulness of the CSP in the determination of the enantiomeric purity of optically active cathinone and in the preparative resolution of racemic cathinone was demonstrated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / isolation & purification
Chromatography, High Pressure Liquid / instrumentation
Chromatography, High Pressure Liquid / methods*
Crown Ethers / chemistry*
Ketones / isolation & purification*
Naphthalenes / chemistry*
Stereoisomerism
Temperature

Substances

(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6
Alkaloids
Crown Ethers
Ketones
Naphthalenes
cathinone