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A facile stereospecific synthesis of the [2H6]-isopropyl-labelled metoprolol enantiomers from (2r)- and (2S)-glycidyl 3-nitrobenzenesulfonate

✍ Scribed by Satya S. Murthy; Wendel L. Nelson

Publisher: John Wiley and Sons
Year: 1990
Tongue: French
Weight: 263 KB
Volume: 28
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580281208

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✦ Synopsis

Abstract

Enantiomers of metoprolol containing six deuterium atoms in the isopropyl methyl groups were prepared in two steps from the sodium salt of 4‐(2‐methoxyethyl)phenol (3) and the commercially available (2__R__)‐ and (2__S__)‐glycidyl 3‐nitrobenzenesulfonates [(2__R__)‐2 and (2__S__)‐2]. The resulting (2__R__)‐ and (2__S__)‐epoxides were opened using [^2^H~6~]‐isopropylamine. The enantiomeric excesses were 93 and 95% for the deuterated (2__R__)‐ and (2__S__)‐enantiomers of metoprolol [(2__R__)‐1 and (2__S__)‐1], respectively, as determined by chiral column HPLC.

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