Erowid References Database
Waldman SR, Monte AP, Bracey A, Nichols DE.
“One-Pot Claisen Rearrangement / O-Methylation / Alkene Isomerization in the Synthesis of Ortho-Methoxylated Pheylisopropylamines”.
Tetrahedron Letters. 1996;37(44):7789-1892.
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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.
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