Methanol → 5-Bromo-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

To a 100 mL round-bottomed flask was added 5-bromo-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline (1.18 g, 3332 μmol, from step 2), MeOH (5 mL), sodium borohydride (117 μL, 3332 μmol, Aldrich). The reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with water (20 mL), saturated NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 40% EtOAc/hexanes to give 5-bromo-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline. MS (ESI pos. ion) m/z: 356 (M+1).

Provenance & Evidence