Gram-Scale, Chemoselective Synthesis Of N-[2-(5-Hydroxy-1h-Indol-3-Yl)Ethyl]-2-Oxopiperidine-3-Carboxamide (Hioc)
TETRAHEDRON LETTERS(2015)
Abstract
N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-2-oxopiperidine-3-carboxamide (HIOC) is a potent activator of the TrkB receptor in mammalian neurons and of interest because of its potential therapeutic uses. In the absence of a commercial supply of HIOC, we sought to produce several grams of material. However, a synthesis of HIOC has never been published. Herein we report the preparation of HIOC by the chemoselective N-acylation of serotonin, without using blocking groups in the key acylation step. (C) 2015 Elsevier Ltd. All rights reserved.
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Key words
Amide synthesis, Chemoselectivity, Decarboxylation, Kinase activation, Serotonin
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