1-Phenethylamine, (+)- → HCID 25263535, compound

Participants

Reaction Steps

A 20 mL vial was charged with (R)-1-phenylethanamine 45 (0.135 g, 1.11 mmol), 5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde 74 (0.200 g, 0.740 mmol), 5 mL of DCE, 3 drops of concentrated AcOH, and sodium triacetoxyborohydride (0.314 g, 1.48 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 10 mL of saturated aqueous NaHCO3 and the mixture was extracted with CH2Cl2. The combined extracts were dried and concentrated. Purification via column chromatography on silica gel (1% to 6% MeOH in DCM) gave (1R)—N-({5-methoxy-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)-1-phenylethanamine 75. Mass spectrum: calculated for C20H20F3N3O 375.2; found 376.2 (M++1).

Provenance & Evidence