[BH4-].[Na+].O.C(=O)(O)[O-].[Na+].[F:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]=[C:17]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1>C(OCC)(=O)C>[F:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][NH:16][CH:17]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1A solution of 7-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (0.6 g, 2.1 mmol) in methanol (10 mL) from step 2 was cooled to 0° C. and sodium borohydride (0.2 g, 6.2 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 (10 mL) and concentrated to yield a light-yellow residue which was dissolved in ethyl acetate (40 mL), water (10 mL), and saturated sodium bicarbonate (20 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 7-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline as a pale-yellow solid. MS (ESI pos. ion) m/z: 296 (M+H).
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