A Pratical Synthesis of Optically Active Atenolol from Chiral Epichlorohydrin

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

doi:10.1248/cpb.45.412

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

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Keywords: optically active atenolol, optically active epichlorohydrin, benzyltrimethylammonium chloride, β-adrenergic blocking agent

JOURNAL FREE ACCESS

1997 Volume 45 Issue 2 Pages 412-414

DOI https://doi.org/10.1248/cpb.45.412

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Abstract

The synthesis of (R)- and (S)-atenolol (1) was achieved in two steps starting from p-hydroxyphenylacetamide (2). Both enantiomers of the glycidyl ether 4 were synthesized from 2 and (R)- and (S)-epichlorohydrin (3) using an alkali metal hydroxide and/or BTA (benzyltrimethylammonium chloride), respectively. Subsequent treatment of 4 with isopropylamine afforded atenolol (1) with excellent enantiomeric excess (>98% ee).

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