By Hyun Cho, Hayden George

Faculty Mentor: Dr. Davis Oldham

Abstract

Multiple analogues for potential tuberculosis (TB) treatment were proposed due to their potential as KasA inhibitors, and a variation was selected for synthetic analysis. A multistep synthesis was thus developed and enacted in an effort to yield 1-(pyrenylmethyl)-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol (1). Starting from 1-bromo-3-(trifluoromethyl)benzene and 1-benzyl-4-piperidone, a Grignard reaction was performed at reflux and extracted; multiple attempts were required due to the reaction’s sensitivity to moisture. The benzyl protecting group was removed utilizing palladium on carbon catalyst in the presence of ammonium formate under reflux and reductive amination will then be carried out to afford 1. The product will be characterized by GC-MS and IR to confirm the desired product formation.