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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
Weitere Informationen
Publikationsverlauf
Received
31 August 2010
Publikationsdatum:
09. November 2010 (online)


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