Water → HCID 59536348, compound

Participants

Reaction Steps

A solution of 6-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (2.6 g, 8.9 mmol) in methanol (50 mL) from step 2 was cooled to 0° C. and sodium borohydride (1.0 g, 2.7 mmol) was added in small portions over 5 min and the reaction mixture was stirred at RT for 16 h. The reaction was quenched with ethyl acetate (20 mL) and concentrated to yield a reddish-yellow residue which was taken up in ethyl acetate (100 mL), water (30 mL), and saturated sodium bicarbonate (30 mL). After stirring for 15 min, it was transferred to a separatory funnel, the organic layer was separated, dried over anhydrous sodium sulfate, and concentrated to yield the crude product. The crude product was purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 6-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline as a pale-yellow solid. MS (ESI pos. ion) m/z: 296 (M+H).

Provenance & Evidence