Gram-scale, chemoselective synthesis of N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-oxopiperidine-3-carboxamide (HIOC). Issue 23 (3rd June 2015)

• Record Type: Journal Article
• Authors: Setterholm, Noah A.; McDonald, Frank E.; Boatright, Jeffrey H.; Iuvone, P. Michael
• Is Part Of: Tetrahedron letters. Volume 56:Issue 23(2015)
• Page Start: 3413
• Page End: 3415
• Publication Date: 2015-06-03
• Subjects: ZIMKJLALTRLXJO-UHFFFAOYSA-N -- HQSIETYOWKHBCH-UHFFFAOYSA-N; Amide synthesis -- Chemoselectivity -- Decarboxylation -- Kinase activation -- Serotonin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.167
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: N -[2-(5-Hydroxy-1 H -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.