Preparation of erythro-2-amino-1-phenylpropanol derivative


PURPOSE: To obtain the titled erythro-derivative, useful as pharmaceuticals for the circulatory system, exclusively, in high selectivity, easily, and economically, by reducing an α-aminopropiophenone derivative in the form of salt or in the presence of an acidic substance, with HaBH 4 . CONSTITUTION: An α-aminopropiophenone derivative of formula I (X is H, OH, benzyloxy, or halogen; R 1 and R 2 are H, 1W6C alkyl, aralkyl, or R 1 and R 2 together with a 4W6C group form a nitrogen-containing ring) is reduced in the form of salt or in the presence of an acidic substance (e.g. hydrochloric acid, acetic acid, etc.) with NaBH 4 to give erythro-2-amino-1-phenylpropanol derivative of formula II. EFFECT: The reduction of the hydrochloride of the propiophenone derivative gives the erythro-isomer in an extremely high selectively (erythro/threo is 96.6%/0.2%), in contrast with the reduction of the derivative in the form of free base, in which the ratio of the threo-isomer or the undesirable type of the steric isomers, becomes high. COPYRIGHT: (C)1981,JPO&Japio




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Patent Citations (2)

    Publication numberPublication dateAssigneeTitle
    JP-S4985035-AAugust 15, 1974
    JP-S51141829-ADecember 07, 1976Yoshitomi Pharmaceut Ind LtdProcess for preparing aminoalcohol derivatives.

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Cited By (1)

    Publication numberPublication dateAssigneeTitle
    EP-0387605-A2September 19, 1990Bayer AgProcédé pour la préparation stéréosélective de S,S ou R,R-bêta-aminoalcools optiquement actifs