Triethylamine → Tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate J, 8.45 g, 20.80 mmol) and platinum(IV) oxide (0.472 g, 2.080 mmol) in 40 mL MeOH was placed under 45 psi (4559.6 kpa) H2 for 2 hours. The reaction mixture was filtered through a plug of diatomaceous earth and was concentrated. The resulting residue was taken up in 10 mL THF, was treated with di-tert-butyl dicarbonate (10.40 ml, 10.40 mmol) followed by triethylamine (2.90 ml, 20.80 mmol) and was allowed to stir for 4 hours. Concentration and purification of the resulting residue by silica gel column chromatography (0 to 10% EtOAc/heptane) gave tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylate (4.812 g, 11.79 mmol) as a clear oil. [M+Na]+=432.0

Provenance & Evidence