Potassium Carbonate → HCID 59536424, compound

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Reaction Steps

To a solution of (4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (240 mg, 0.87 mmol, example 9 (step 3) and DIEA (151 μL, 0.87 mmol) in DCM (3 mL) was added 1-chlorocarbonyl-1-methylethyl acetate (125 μL, 0.87 mmol) slowly. After addition, the mixture was stirred at RT for 16 h. Then, an additional amount of 1-chlorocarbonyl-1-methylethyl acetate (60 μL) was added and the mixture was stirred at RT for 16 h. Then, H2O (2 mL) was added and the mixture was stirred at RT for 10 min. The organic layer was collected and the aqueous layer was extracted with EtOAc (2×3 mL). The combined organic extracts were then dried over MgSO4 and concentrated to give a crude intermediate. Then, the crude intermediate was dissolved in MeOH (10 mL), and then potassium carbonate (239 mg, 1.7 mmol) was added. The resulting mixture was then stirred at RT for 16 h. Then, the mixture was filtered and the solid was washed with DCM (2×5 mL). The combined filtrates were concentrated and the residue was purified by silica gel flash column chromatography (0%-400% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 364 (M+H).

Provenance & Evidence