title: Gram-scale, chemoselective synthesis ofN-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-oxopiperidine-3-carboxamide (HIOC).
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 chemoselectiveN-acylation of serotonin, without using blocking groups in the key acylation step.
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive NE, Atlanta, GA 30322 USA.
authors.forename: Noah A
authors.initials: NA
authors.lastname: Setterholm
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive NE, Atlanta, GA 30322 USA.
authors.forename: Frank E
authors.initials: FE
authors.lastname: McDonald
authors.affiliation: Department of Ophthalmology, Emory University School of Medicine, 1365B Clifton Road NE, Atlanta, GA 30322 USA ; Rehabilitation R & D Center, Atlanta VA Medical Center, Decatur, GA USA 30033 USA.
authors.forename: Jeffrey H
authors.initials: JH
authors.lastname: Boatright
authors.affiliation: Department of Ophthalmology, Emory University School of Medicine, 1365B Clifton Road NE, Atlanta, GA 30322 USA ; Department of Pharmacology, Emory University School of Medicine, 1510 Clifton Road NE, Atlanta, GA 30322 USA.
authors.forename: P Michael
authors.initials: PM
authors.lastname: Iuvone
keywords: activation; amide; chemoselectivity; decarboxylation; kinase; serotonin; synthesis