鎮痙作用を有する芳香族塩基性エーテルに関する研究(第5報)2-Methyl-1-phenyl-3-piperidinopropyl Phenyl Ether誘導体の立体化学

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Configurational analyses for diastereoisomers of 3-dimethylamino-2-methyl-1-phenylpropyl phenyl ether (1a), 2-methyl-1-phenyl-3-piperidinopropyl phenyl ether (1b), 2-methyl-3-(2-methylpiperidino)-1-phenylpropyl phenyl ether (1c), and their quaternary bases were made by their nuclear magnetic resonance spectra. It was found that the chemical shifts of H^<(1)> in the erythro-isomers appeared at a lower field and their coupling constants, JH^<(1)>H^<(2)>, were smaller than those of the corresponding threo-isomers. The threo-amino chlorides were obtained from the erythro-amino alcohols with inversion, while erythro-amino chlorides were obtained together with threo-amino chlorides from the threo-amino alcohols. These configurational arrangements were retained in the ether condensation reactions.
1973-09-25