唐恢同, 柴文刚, 张廉, 荆会荣, 耿一芳, 范丽华, 张强, 彭和平. (R)-1-羟基-1-(间-羟基苯基)-丙酮肟的电化学还原——合成阿拉明的新方法J. 药学学报, 1981, 16(6): 440-444.
引用本文: 唐恢同, 柴文刚, 张廉, 荆会荣, 耿一芳, 范丽华, 张强, 彭和平. (R)-1-羟基-1-(间-羟基苯基)-丙酮肟的电化学还原——合成阿拉明的新方法J. 药学学报, 1981, 16(6): 440-444.
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Tang Huitong, Ghai Wengang, Zhang Lian, Jing Huirong, Geng Yifang, Fan Lihua, Zhang Qiang , Peng Heping, . ELECTROCHEMICAL REDUCTION OF (R)-1-HYDROXYL-1-(m-HYDROXYLPHENYL)-ACETONE OXIME——A NEW METHOD OF PREPARING METARAMINOLJ. Acta Pharmaceutica Sinica, 1981, 16(6): 440-444.
Citation: Tang Huitong, Ghai Wengang, Zhang Lian, Jing Huirong, Geng Yifang, Fan Lihua, Zhang Qiang , Peng Heping, . ELECTROCHEMICAL REDUCTION OF (R)-1-HYDROXYL-1-(m-HYDROXYLPHENYL)-ACETONE OXIME——A NEW METHOD OF PREPARING METARAMINOLJ. Acta Pharmaceutica Sinica, 1981, 16(6): 440-444.
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(R)-1-羟基-1-(间-羟基苯基)-丙酮肟的电化学还原——合成阿拉明的新方法

ELECTROCHEMICAL REDUCTION OF (R)-1-HYDROXYL-1-(m-HYDROXYLPHENYL)-ACETONE OXIME——A NEW METHOD OF PREPARING METARAMINOL

    摘要
  • 摘要: 本文报道了将(R)-1-羟基-1-(间-羟基苯基)-丙酮肟(Ⅳ)在弱酸介质中,以汞或铅做阴极,经电解还原立体选向地得到(1R,2S)-1-(间-羟基苯基)-2-氨基丙醇-1,为常用的拟交感神经药物阿拉明及其类似化合物的合成提供了一个新的途径。本文讨论了肟Ⅳ矿的极谱行为并报道了肟Ⅳ在电解时同时发生的羟基还原断裂。

     

    Abstract: (R)-1-Hydroxyl-1-(m-hydroxylphenyl)-acetone was converted in acidic medium to its oxime (Ⅳ), which was then electrolytically and stereoselectively reduced to give(1R, 2S)-1-(m-hydroxylphenyl)-2-aminopropanol-1, in the same medium. Mercury cathod yielded better result than lead cathod. Polarographic behaviour of the oxime Ⅳ is discussed and reductive cleavage of the hydroxyl group in Ⅳ at the cathod is noted.

     

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