Water → 4-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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To a solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (200 mg, 0.721 mmol, example 9 (step 3) and DIEA (126 μL, 0.721 mmol) in DCM (4 mL) was added 4-nitrophenyl chloroformate (145 mg, 0.721 mmol). The resulting mixture was stirred at RT for 16 h. Then, H2O (10 mL) was added and the mixture was extracted with DCM (2×5 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel flash column chromatography (0%-50% EtOAc/hexane) to give the title compound as a white oil. MS (ESI, positive ion) m/z: 443 (M+H).

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