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

作者：Setterholm Noah A; McDonald Frank E^*; Boatright Jeffrey H; Iuvone P Michael

来源：Tetrahedron Letters, 2015, 56(23): 3413-3415.

DOI：10.1016/j.tetlet.2015.01.167

• Amide synthesis
• Chemoselectivity
• Decarboxylation
• Kinase activation
• Serotonin

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.

• 出版日期2015-6-3