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

Tetrahedron Lett

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.

Published: June 2015

-[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 -acylation of serotonin, without using blocking groups in the key acylation step.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4445863PMC
http://dx.doi.org/10.1016/j.tetlet.2015.01.167DOI Listing

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

Tetrahedron Lett

June 2015

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.

-[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.

View Article and Find Full Text PDF

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