(－)-2-(N-正丙基氨基)-5-羟基四氢化萘的合成

以1,6-二甲氧基萘为原料，经Na/C₂H₅OH还原生成5-甲氧基-2-四氢萘酮，与正丙胺还原胺化生成外消旋化合物2-(N-正丙基氨基）-5-甲氧基四氢化萘，经拆分得到手性的化合物(－)-2-（N-正丙基氨基）-5-甲氧基四氢化萘，再去甲基反应得到化合物(－)-2-（N-正丙基氨基）-5-羟基四氢化萘。采用元素分析、红外光谱、¹H-NMR和¹³C-NMR表征了中间体和产物的分子结构。通过合成工艺的研究，得到较好的工艺条件，反应总收率达16.8%。采用一步法的还原胺化反应，不仅简化了反应步骤，而且收率提高了16.2%。

Synthesis of (-) -5-hydroxy-2- (N-propylamino) tetralin

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.