The Journal of Organic Chemistry

A new synthesis of primary aliphatic amines by N, N-didebenzylation. Synthesis of a pirmenol (CI-845) metabolite

CF Purchase, OP Goel

Index: Purchase II, Claude F.; Goel, O. P. Journal of Organic Chemistry, 1991 , vol. 56, # 1 p. 457 - 459

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Citation Number: 12

Abstract

Pirmenol (CI-845)(la) is an antiarrhythmic agent currently in clinical trials.'For the synthesis of one of the pirmenol metabolites 1 b, we were unsuccessful in using the Gabriel synthesis2 to make the primary amine functionality. When we added 2-pyridyllithium to phthalimide 2, no addition product was isolated. Alternative Gabriel reagents have been developed, but they too have potential drawbacks. They are either pho~ poramidate,~~ or derivatives that ...