Z. Hong, Kbd Pharmaceutical
2007
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Journal
Journal of Beijing University of Chemical Technology
Abstract
Reduction of 1,6-dimethoxynaphthalene with Na/EtOH afforded 5-methoxy-2-tetralone. Racemic 5-methoxy-2-(N-propylamino)tetralin was subsequently prepared by a reductive amination reaction using n-propylamine and the racemic mixture successfully resolved to give the chiral compound (-)-5-methoxy-2-(N-propylamino)tetralin, which was finally converted to (-)-5-hydroxy-2-(N-propylamino) tetralin via a demethylation reaction. By means of a systematic study, the optimum conditions were identified; the maximum observed overall yield was 16.8%. Furthermore it was found that by using a one-step reductive amination reaction, not only was the synthesis shortened, but the yield was enhanced by 16.2%. Structures of intermediate compounds and the final product were characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectroscopy.