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Synfacts 2011(8): 0822-0822  
DOI: 10.1055/s-0030-1260673
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Suvorexant

Contributor(s): Philip Kocienski
N. A. Strotman*, C. A. Baxter, K. M. J. Brands, E. Cleator, S. W. Krska, R. A. Reamer, D. J. Wallace, T. J. Wright
Merck Research Laboratories, Rahway, USA and Merck Sharp & Dohme Research Laboratories, Hoddesdon, UK
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

Suvorexant (MK-4305) is a selective dual orexin antagonist that has entered phase III clinical trials for the treatment of insomnia. The synthesis of suvorexant depicted incorporates the first example of an intramolecular asymmetric reductive amination of a dialkyl ketone with an ­aliphatic amine (F → G → I) using a variant of ­Noyori’s RuCl(p-cymene)(ArSO2DPEN) transfer hydrogenation catalyst.