1-Methyl-3,4-dihydro-β-carboline (1) was C-acylated with optically active sulfinyl derivatives (2) into the 1-methyl group. Reduction of the C=N double bond resulted in diastereomers (4, 5) of different ratios. After separation of diastereomers and removal of the chiral sulfinyl moiety, enantiomers of 1-methyl-1,2,3,4-tetrahydro-β-carboline (6) were obtained from different enantiomeric excess. The diastereomers were separated by normal phase chromatography. It was proven that the resolution efficiency was much better with this type of separation method compared with very popular reversed phase chromatography. Embedded reversed phase column (Supelcosil ABZ + Plus) gave higher resolution than conventional C-18 stationary phases and monoliths (Chromolith Performance RP-18e), but retention time is high and low solubilities of derivatives caused detection problems and base line noise.
|Number of pages||13|
|Journal||Journal of Liquid Chromatography and Related Technologies|
|Publication status||Published - okt. 25 2004|
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmaceutical Science
- Clinical Biochemistry