Synthesis of 4'-hydroxypropranolol sulfate, a major non-. beta.-blocking propranolol metabolite in man

…, HB Daniell, TE Gaffney, DR Knapp

Index: Oatis, John E.; Walle, T.; Daniell, H. B.; Gaffney, T. E.; Knapp, D. R. Journal of Medicinal Chemistry, 1985 , vol. 28, # 6 p. 822 - 824

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Citation Number: 23

Abstract

4'-Hydroxypropranolol sulfate (8) was recently identified as a major metabolite of propranolol (Inderal). In order to confirm the structure and to further study disposition and biological activity, we have synthesized 8 with use of 1, 4-naphthoquinone (1) as the starting material. Reduction and alkylation with benzyl iodide gave 4-(benzyl-oxy) naphthol (3). Sulfation and chlorosulfuric acid in Nfl-dimethylaniline gave potassium l-(benzyloxy)-4- ...