Gram-scale, chemoselective synthesis of N-[2-(5-hydroxy-1H-indol-3-yl) ethyl]-2-oxopiperidine-3-carboxamide (HIOC)

NA Setterholm, FE McDonald, JH Boatright… - Tetrahedron letters, 2015 - Elsevier
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.