Convenient Preparation of Enantiopure Atenolol by Means of Preferential Crystallization

Kazuhiro KITAORI; Yoshikazu TAKEHIRA; Yoshiro FURUKAWA; Hiroshi YOSHIMOTO; Junzo OTERA

doi:10.1248/cpb.46.505

Kazuhiro KITAORI, Yoshikazu TAKEHIRA, Yoshiro FURUKAWA, Hiroshi YOSHIMOTO, Junzo OTERA

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Keywords: optically active atenolol, optically active epichlorohydrin, preferential crystallization, β-adrenergic blocking agent

JOURNAL FREE ACCESS

1998 Volume 46 Issue 3 Pages 505-507

DOI https://doi.org/10.1248/cpb.46.505

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Abstract

(R)- or (S)-Atenolol (1) in enantiopure form was prepared in an extremely simple way. Atenolol of ca. 95% ee was prepared in one-pot from p-hydroxyphenylacetamide (2) and (R)- or (S)-epichlorohydrin (3). Then, preferential crystallization of the Bronsted's acid salts of the resulting atenolol improved the enantiomeric purity up to 99.8% ee.

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