Diiodomethane → 1-tert-Butoxycarbonyl-2(S)-(2-cyclopropyloxyethyl)-4-(1-naphthoyl)piperazine

1-tert-Butoxycarbonyl-2(S)-(2-vinyloxyethyl)-4-naphthoylpiperazine (0.107 g, 0.261 mmol) was dissolved in ether (5 mL) under an argon atmosphere. To this solution was added diiodomethane (0.042 mL, 0.522 mmol) and diethylzinc (0.39 mL, 1M in hexane, 0.39 mmol). The reaction was refluxed for 1 h. The reaction was quenched with water, and extracted with ethyl acetate. The organic extracts were washed with water, saturated sodium chloride, and dried over magnesium sulfate. The title compound was obtained as an oil.