Water → HCID 69885958, compound

Participants

Reaction Steps

To a solution of AlCl3 (48.7 mg, 0.36 mmol) in dry CH2Cl2 (1 mL) at 0° C., tetrahydroisoquinoline (88 μl, 0.70 mmol) in CH2Cl2 (1 mL) was added dropwise. The mixture was stirred at room temperature for 10 min, and then ethyl (1SR, 2SR, 5RS, 6RS) 3-tert-butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate (96 mg, 0.28 mmol) in dry CH2Cl2 (1 mL) was added. After stirring at room temperature for 3 h, a mixture of ice and water was added. The layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash chromatography (hexane/ethyl acetate 2/1) to give 95 mg of the desired compound (71% yield).

Provenance & Evidence