Sodium borohydride → 1-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (4.69 g, 17 mmol) in MeOH (24 mL) was added sodium borohydride (1.94 g, 51.1 mmol) slowly at 0° C. Then, the mixture was stirred at 0° C. for 15 min and at RT for 2 h. The solvent was then removed and H2O (20 mL) was added to the residue. A saturated NaHCO3 solution (150 mL) was added slowly and the mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was mixed with silica gel (4:1; residue:silica gel) and purified by silica gel chromatography (20%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 278 (M+H).

Provenance & Evidence