Acetic Acid → (R)-methyl 1-(2-(5-methylisoxazole-3-carboxamido)-4-((1-phenylethylamino)methyl)phenyl)piperidine-4-carboxylate

Participants

Reaction Steps

To a solution of methyl 1-(4-formyl-2-(5-methylisoxazole-3-carboxamido)phenyl)piperidine-4-carboxylate 60 (0.268 g, 0.72 mmol) in DCE (10 mL) was added acetic acid (0.045 mL, 0.78 mmol), (R)-1-phenylethanamine (0.11 mL, 0.88 mmol), and NaBH(OAc)3 (0.186 g, 0.88 mmol). The reaction mixture was stirred at room temperature for 15 h and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 70% to 100% EtOAc in hexanes) gave (R)-methyl 1-(2-(5-methylisoxazole-3-carboxamido)-4-((1-phenylethylamino)methyl)phenyl)piperidine-4-carboxylate 61 (0.230 g, 67% yield) as a white solid. Mass spectrum: calculated for C27H32N4O4 476.2. found 477.3 (M++1).

Provenance & Evidence