3, 4-Catechol derivative of propranolol, a minor dihydroxylated metabolite

WL Nelson, MJ Bartels, PJ Bednarski…

Index: Nelson; Bartels; Bednarski; Zhang; Messick; Horng; Ruffolo Jr. Journal of Medicinal Chemistry, 1984 , vol. 27, # 7 p. 857 - 861

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Citation Number: 10

Abstract

The 0, O-dibenzyl ether of the 3, 4-catechol derivative of propranolol (1 1) was prepared to determine whether the catechol is a product of metabolic hydroxylation. 4-(Allyloxy)-1, 2- naphthoquinone (5) was reduced with sodium dithionite and alkylated with benzyl chloride to produce ether 7. Osmium tetroxide oxidation of 7 afforded glycol 8. Subsequent monotosylation, oxirane formation with KOH, and opening with isopropylamine afforded ...