Chemical and Pharmaceutical Bulletin p. 412 - 414 (1997)
Update date:2022-08-11
Topics:
Kitaori, Kazuhiro
Takehira, Yoshikazu
Furukawa, Yoshiro
Yoshimoto, Hiroshi
Otera, Junzo
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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