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.
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.