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Stereospecific synthesis of specifically deuterated metoprolol enantiomers from chiral starting materials

โœ Scribed by H. Umesha Shetty; Satya S. Murthy; Wendel L. Nelson

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
582 KB
Volume
27
Category
Article
ISSN
0022-2135

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โœฆ Synopsis

Enantiomers of metoprolol (1) containing six deuterium atoms in the isopropyl methyl groups [(Ui-21, two deuterium atoms at C-2 and C-6 of the aromatic ring C(2S1-31, and two deuterium atoms at C-3 of the propanolamine side chain C(2S)-41 were prepared. Chiral2,2-dimethyl-1,3-dioxolane-4-methanols [(4R)-5 and (4s)-51 were key synthons. Sources of deuterium were [2H61-isopropylamine, 4-(2-methoxyethyl)-2,6-12H2l-phenol(12), prepared by 2HC@H20 exchange, and (4S)-2,2-dimethyl-1,3-dioxolane-4-~~H~1-4-methanol(19), prepared by LiA12Hq reduction of (4S)-methyl2,2-dimethyl-1,3-dioxolane-4-carboxylate. Enantiomeric excess was greater than 94% for each of the prepared enantiomers, as determined independently by 1H NMR spectroscopy on diastereomeric derivatives and by chiral column HPLC.

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