Facile synthesis of suvorexant, an orexin receptor antagonist, via a chiral diazepane intermediate

A facile synthesis of suvorexant, an orexin receptor antagonist, is described. The key intermediate 6 was prepared from R-3-aminobutyric acid through protection, condensation, deprotection, cyclization, and hydrogenation steps. The title product was obtained with a total yield of 31% (>99% ee) after eight linear steps using commercially available raw materials.

Suvorexant was obtained with a total yield of 31% after eight linear steps using commercially available R-3-aminobutyric acid.Figure optionsDownload as PowerPoint slide