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A facile stereospecific synthesis of the [ 2 H 6 ]‐isopropyl‐labelled metoprolol enantiomers from (2 r )‐ and (2 S )‐glycidyl 3‐nitrobenzenesulfonate
Author(s) -
Murthy Satya S.,
Nelson Wendel L.
Publication year - 1990
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580281208
Subject(s) - chemistry , isopropylamine , enantiomer , stereospecificity , isopropyl , metoprolol , deuterium , phenol , stereochemistry , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics , medicine , cardiology
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.