To a solution of tert-butyl 3,3-difluoro-4-oxopiperidine-1-carboxylate (0.250 g, 1.06 mmol) in CH2Cl2 (4.5 mL) was added benzylamine (0.13 mL, 1.17 mmol) and sodium triacetoxyborohydride (0.356 g, 1.59 mmol) and the solution was stirred at rt for 22 h. The reaction mixture was treated with sat. aq. Na2CO3 and extracted with EA (3×50 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. The residue was purified by FC (Heptane/EA, 1:1) to give tert-butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate. LC-MS-conditions 08: tR=0.65 min; [M+H]+=327.32.
