High-performance liquid chromatographic enantioseparation of methanobenzazocines.
Chiral recognition and resolution of methanobenzazocines was investigated by HPLC using polysaccharide, Pirkle-type, native and derivatized beta-cyclodextrin chiral stationary phases. Enantioseparation of phenyl substituted 2,6-methanobenzazocines was achieved with multiple chiral stationary phases throughout the classes described. Chiral resolution of the enantiomers of 1,5-methano-3-methyl-6-oxo-1,2,3,4,5,6-hexahydro-3-benzazocine was produced on both polysaccharide and Pirkle-type phases. In the case of 1,5-methano-3-methyl-6-phenyl-1,2,3,4,5,6-hexahydro-3-benzazocine only a dinitrophenyl substituted beta-cyclodextrin produced a separation of enantiomers.
Barker
William M
WM
Department of Chemistry, Adolor Corporation, 700 Pennsylvania Drive, Exton, PA 19341, USA.
Worm
Karin
K
Dolle
Roland E
RE
D001575:Benzomorphans / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D013237:Stereoisomerism
D001575:Benzomorphans