Enantioseparation of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline on Polysaccharide-Based Chiral Stationary Phases

Abstract

The enantiomers of 1-phenyl-1,2,3,4-tetrahydroisoquinoline have been directly separated on polysaccharide-based chiral stationary phases (CSPs). The normal phase separation of (S)-and (R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline was accomplished by screening of the immobilized Chiralpak IC column with different eluents. The effect of mobile phase type on retention, selectivity and resolution was studied. 2-Propanol or ethanol/n-hexane/ ethanolamine mixtures were applied as mobile phases by screening of following polysaccharide-based immobilized (Chiralpak IA, Chiralpak IC) and coated (Lux Cellulose-1, Lux Cellulose-2, Lux Amylose-2) CSPs. Polar organic and reversed-phase conditions were also tested for direct enantioseparation of 1-phenyl-1,2,3,4-tetrahydroisoquinoline.

High‐performance liquid chromatographic enantioseparation of amino alcohol analogues possessing 1,2,3,4‐tetrahydroisoquinoline skeleton on polysaccharide‐based chiral stationary phases

“…The HPLC separation of salsolinol enantiomers has been achieved through the application of various CSPs (Deng et al ., ; Baum and Rommelspacher, ; Rommelspacher et al ., ; Stammel and Thomas, ; Stammel et al ., ; Zhang et al ., , ; de los Angeles Juricic et al ., ). The normal‐phase HPLC separation of phenyl‐ and naphthol‐substituted Tiq analogues has been accomplished using polysaccharide‐based CSPs (Kazoka et al ., ; Ilisz et al ., ).…”

High‐performance liquid chromatographic and subcritical fluid chromatographic separation of α‐arylated ß‐carboline, N‐alkylated tetrahydroisoquinolines and their bioisosteres on polysaccharide‐based chiral stationary phases

“…For the separation of isoquinoline‐like stereoisomers, HPLC measurements were performed with the use of ß ‐cyclodextrin and its derivatives as chiral mobile phase additives or as CSP . In recent years, polysaccharide‐ and Cinchona alkaloid‐based CSPs were applied for the enantioseparation of isoquinolines. It is important to mention that besides CE, GC, and HPLC, SFC is becoming an increasingly powerful technique for the enantioseparation of various chiral compounds .…”

High‐performance liquid chromatographic enantioseparation of naphthol‐substituted tetrahydroisoquinolines on polysaccharide‐based chiral stationary phases

“…The direct separation of salsolinol enantiomers on β ‐cyclodextrin‐containing chiral stationary phases (CSPs) was achieved with a GC (Liu et al ., ) or HPLC method (Deng et al ., ; Baum and Rommelspacher, ; Rommelspacher et al ., ; Stammel and Thomas, ; Stammel et al ., ; Zhang et al ., , ). The normal‐phase separation of ( S )‐ and ( R )‐1‐phenyl‐1,2,3,4‐Tiq was accomplished using an immobilized polysaccharide‐based Chiralpak IC column with different propan‐2‐ol or ethanol– n ‐hexane–ethanolamine mobile phases (Kazoka et al ., ). After chiral column separation 750 MHz H‐1 NMR spectroscopy was used on‐line to identify the enantiomeric pairs of atracurium besylate (Mistry et al ., ).…”