Phenethyl bromide → 1-(Benzyloxycarbonyl)-2-(2-phenylethyl)pyrazolidin-3-one

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Reaction Steps

Sodium hydride (562 mg, 14.1 mmol, 60% mineral oil dispersion) is added to a solution of 1-(benzyloxycarbonyl)pyrazolidin-3-one (2.81 g, 12.8 mmol, prepared similarly to that described in J. Org. Chem. 1990, 55, 6037) and DMF (37 mL) at 0° C. The solution is stirred for 30 minutes and then (2-bromoethyl)benzene (1.90 mL, 13.9 mmol) is added. The solution is stirred at 0° C. for 1 hour and 16 hours at room temperature. Aqueous workup (EtOAc, brine, MgSO4) and purification by flash chromatography (2:1→1:1 hexane:EtOAc) gives 1.58 g (38%) of the title compound as an oil.

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