Acetic Acid → HCID 59803184, compound

Participants

Reaction Steps

To a solution of methyl 1-(2-chloro-5-formylphenyl)piperidine-4-carboxylate 68 (0.180 g, 0.64 mmol) in DCE (3 mL) was added (R)-1-phenylethanamine (0.10 mL, 0.79 mmol), acetic acid (0.040 mL, 0.69 mmol), and NaBH(OAc)3 (0.168 g, 0.79 mmol). The reaction mixture was stirred at room temperature for 20 h, quenched with saturated NaHCO3, and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 (1×), brine (1 x), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes) gave (R)-methyl 1-(2-chloro-5-((1-phenylethylamino)methyl)phenyl)piperidine-4-carboxylate 69 (0.215 g, 87% yield) as a colorless oil. Mass spectrum: calculated for C22H27ClN2O2 386.2. found 387.2 (M++1).

Provenance & Evidence