Acetic Acid → HCID 25265627, compound

Participants

Reaction Steps

To a solution of 1-phenyl-1H-pyrazole-5-carbaldehyde 38 (0.517 g, 3 mmol) in DCE (10 mL) at room temperature was added (R)-1-(naphthalen-1-yl)ethanamine 39 (0.625 g, 4 mmol), acetic acid (0.208 g, 3 mmol), and NaBH(OAc)3 (0.946 g, 4 mmol). The reaction mixture was stirred at room temperature for 18 h, quenched with saturated NaHCO3, diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 20% to 70% EtOAc in hexanes) gave (1R)-1-(1-naphthalenyl)-N-((1-phenyl-1H-pyrazol-5-yl)methyl)ethanamine 40. Mass spectrum: calculated for C22H21N3 327.2; found 328.2 (M++1).

Provenance & Evidence