Sodium borohydride → HCID 59536265, compound

Participants

Reaction Steps

To a stirred solution of 1-(3,4-difluorophenyl)-3,4-dihydroisoquinoline (1.34 g, 5.51 mmol) in 20 mL of MeOH, sodium borohydride (0.4366 g, 11.5 mmol) was added. The mixture was stirred for 1 h. MeOH was evaporated and the residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford a white solid. The crude product was purified by silica gel chromatography (0-5% iso-propanol (with 10% ammonium hydroxide) in CHCl3) to afford the title compound as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 6.99-7.22 (m, 6H) 6.74 (d, J=7.60 Hz, 1H) 5.08 (s, 1H) 3.18-3.32 (m, 1H) 2.96-3.18 (m, 2H) 2.76-2.90 (m, 1H).

Provenance & Evidence