tert-butyl N-(5-(trifluoromethyl)pyridin-3-yl)carbamate → tert-butyl N-[(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamate

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To a solution of tert-butyl 5-(trifluoromethyl)pyridin-3-ylcarbamate (3 g, 14 mmol) in glacial acetic acid (50 mL) was added 5% Rhodium on active carbon (0.5 g) and Platinum(IV) oxide (0.5 g) in the hydrogenation steel bomb. The mixture was sealed and hydrogenated at 200 psi and 70° C. for 48 h. the mixture was filtered through Celite and concentrated to give cis-(+/−)-tert-butyl 5-(trifluoromethyl)piperidin-3-ylcarbamate. LCMS (m/z): 269.1 (MH+).

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