High-performance liquid chromatographic enantioseparation of methanobenzazocines |
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Authors: | William M Barker Karin WormRoland E Dolle |
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Institution: | Department of Chemistry, Adolor Corporation, 700 Pennsylvania Drive, Exton, PA 19341, USA |
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Abstract: | Chiral recognition and resolution of methanobenzazocines was investigated by HPLC using polysaccharide, Pirkle-type, native and derivatized β-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 β-cyclodextrin produced a separation of enantiomers. |
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Keywords: | HPLC Chiral separation Enantioselective Benzazocine Benzomorphans Racemic Cyclodextrin Polysaccharide and Pirkle-type chiral stationary phases |
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