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Synthesis 2011(1): 79-82
DOI: 10.1055/s-0030-1258968
DOI: 10.1055/s-0030-1258968
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Novel Synthesis of the Antidepressant Agomelatine
Further Information
Received
31 August 2010
Publication Date:
09 November 2010 (online)
Publication History
Publication Date:
09 November 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201101/lookinside/thumbnails/10.1055-s-0030-1258968-1.jpg)
Abstract
Agomelatine was synthesized from (2-methoxynaphthalene-8-yl)oxoacetic acid in a four-step approach involving borane reduction, semipinacol rearrangement of the resulting diol, aldoxime formation, and Ra-Ni hydrogenation/acetylation in 51% overall yield. The reaction sequence includes a novel one-pot conversion of an aldoxime into an N-acetylamine. The synthetic route could be useful as a new approach towards N-acetylarylethylamines.
Key words
semipinacol rearrangement - aldoxime reduction - catalytic hydrogenation - acylation - medicinal chemistry
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