tert-butyl N-(5-(trifluoromethyl)pyridin-3-yl)carbamate → HCID 59455772, compound

Participants

Reaction Steps

In a 50 mL hastalloy metal reactor, tert-butyl (5-(trifluoromethyl)pyridin-3-yl)carbamate (600 mg, 2.29 mmol) was treated with glacial acetic acid (10 mL), platinum (IV) oxide (250 mg, 1.10 mmol) and rhodium (5 wt. % (dry) on carbon, degussa type, 250 mg, 2.43 mmol) and hydrogenated at 200 psi hydrogen at 70° C. for 23 h. The reaction mixture was cooled to RT and filtered through a 0.45 um acrodisc, washed with MeOH and concentrated under reduced pressure. The residue was treated with EtOAc and 2N NaOH and extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine and dried over MgSO4, filtered and concentrated to afford rac-tert-butyl (5-(trifluoromethyl)piperidin-3-yl)carbamate (490 mg, 1.83 mmol, 80%). MS (ESI, pos. ion) m/z: 269.1 (M+1). The crude material was used in the subsequent step without further purification.

Provenance & Evidence