Ethyl iodoacetate → Ethyl 2-(4-benzyloxycarbonyl-2-oxopiperazino)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-benyloxycarbonylpiperazin-2-one (M.W.=234.26, 2.34 g, 10 mmol) in anhydrous THF (150 mL) at −78° C. under argon was added lithium bis(trimethylsilyl) amide (1 M in THF, 12 mL, 12 mmol) dropwise. The mixture was stirred at −78° C. for 30 min Ethyl iodoacetate (M.W.−214, 2.14 g, 10 mmol) was added to the mixture at −78° C., stirred, warmed up to −10° C., and then kept in the freezer over night. The reaction was quenched by adding 1N HCl (60 mL) and extracted with EtOAc (200 mL+100 mL). The combined organic layers were washed with sat. NaCl three times, dried with MgSO4, and evaporated to give the crude title compound as a yellowish oil. Reversed-phase HPLC purification afforded the pure compound in 81% yield.

Provenance & Evidence