Tetrahedron letters

One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of ortho-methoxylated phenylisopropylamines

SR Waldman, AP Monte, A Bracey, DE Nichols

Index: Waldman, Steve R.; Monte, Aaron P.; Bracey, Ann; Nichols, David E. Tetrahedron Letters, 1996 , vol. 37, # 44 p. 7889 - 7892

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Citation Number: 21

Abstract

An improved synthesis of a potent serotonin agonist 1a and its novel derivative 1b is described, making use of a Claisen rearrangement whose unstable phenolic product is methylated and isomerized in situ. This method may be of general use in the synthesis of o- methoxylated phenethylamine derivatives. The synthesis also includes an unusual, one pot demethylation/primary alcohol bromination with boron tribromide.