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

Participants

Reaction Steps

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (1550 mg, 5590 μmol) and diea (1071 μL, 6149 μmol) in DCM (36 mL) at 0° C. was added 4-nitrophenyl chloroformate (1465 mg, 7267 μmol, Aldrich). After addition, the reaction mixture was stirred at RT for overnight. Then, H2O (60 mL) was added and the mixture was stirred at RT for 15 min. The organic layer was collected and the aqueous was extracted with DCM (1×50 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was then mixed with silica gel (4:1, residue: silica gel) and the solid mixture was purified by silica gel flash column chromatography using ISCO instrument (solid loading, 0%-100% EtOAc/hexane) to give the compound as an off-white solid. MS (ESI, positive ion) m/z: 443 (M+H).

Provenance & Evidence