S. Murthy, W. L. Nelson
Dec 1, 1990
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Journal
Journal of Labelled Compounds and Radiopharmaceuticals
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 (2R)- and (2S)-glycidyl 3-nitrobenzenesulfonates [(2R)-2 and (2S)-2]. The resulting (2R)- and (2S)-epoxides were opened using [2H6]-isopropylamine. The enantiomeric excesses were 93 and 95% for the deuterated (2R)- and (2S)-enantiomers of metoprolol [(2R)-1 and (2S)-1], respectively, as determined by chiral column HPLC.