Journal of medicinal chemistry

Chemical aspects of metoprolol metabolism. Asymmetric synthesis and absolute configuration of the 3-[4-(1-hydroxy-2-methoxyethyl) phenoxy]-1-(isopropylamino)-2- …

HU Shetty, WL Nelson

Index: Shetty, H. Umesha; Nelson, Wendel L. Journal of Medicinal Chemistry, 1988 ,  vol. 31,  # 1  p. 55 - 59

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Citation Number: 28

Abstract

The side chain was elaborated by condensing 4 with (RS)-2, 2-dimethyl-4-[(tosyloxy) methyl]- 1, 3-dioxolane (6). The dioxolane three-carbon electrophile was chosen because a deuteriated form was available1'for subsequent planned work. Hydrolysis of the acetonide afforded diol 1. Its conversion to 3 was effected via tosylation, followed by epoxide formation by adding sodium hydride. Subsequent opening of epoxide 8 with isopropylamine in the ...