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.
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.
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, South Korea.
Hee Jung
HJ
Choi
Jong Sung
JS
Jin
Myung Ho
MH
Hyun
D000470:Alkaloids / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D007659:Ketones / Q000302:isolation & purification*; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
C530035:(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6; D000470:Alkaloids; D043844:Crown Ethers; D007659:Ketones; D009281:Naphthalenes; C023665:cathinone