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Communication | Special issue | Vol 64, No. 1, 2004, pp.61-64
Published online, 9th November, 2004
DOI: 10.3987/COM-04-S(P)37
Synthesis of N-Trifluoroacetyl-2-hydroxynoraporphine by Radical Reaction of p-Quinol Acetate of N-Trifluoroacetyl-1-(2-iodoveratryl)methyl-1,2,3,4-tetrahydro-7-methoxyisoquinolin-6-ol

Akiko Moriya and Osamu Hoshino*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

Radical reaction of p-quinol acetate (8b) of N-trifluroroacetyl-1- (2-iodoveratryl)methyl-1, 2, 3, 4-tetrahydro-7-methoxyisoquinolin-6-ol (7b) using tributyltin hydride gave the corresponding noraporphine (9)(45 %), while that of the bromo congener (8a) failed. Similar reaction of 8b using tris(trimethylsilyl)silane improved the yield (75 %) of 9.