Undergraduate researchers synthesized novel molecules aimed to teach interdisciplinary research skills. The target was to provide compounds that may solve medical challenges and to teach students about the discovery process. The hexahydroazepine ring was used as a replacement for the piperidine ring, which has many links and references in clinical and preclinical research (for example Spiperone 1 ). We then modified the hexahydroazep-4-one with a Horner-Wadsworth-Emmons reaction to afford an a,�-unsaturated ester. Subsequent reductive amination afforded substitution on the nitrogen of the azepine ring. This provided two points of diversity for a small library to be tested in the targeted and phenotypic testing by Lilly's Open Innovation Drug Discovery Project.

Undergraduate chemical education using hexahydroazepine core synthesis for innovation

247th National Meeting (2014)

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