tert-Butyl bromoacetate → tert-Butyl 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

Participants

Reaction Conditions

Reaction Steps

LDA (2.0M, 11.5 mL, 23.0 mmol) is added to a solution of 3-(2-methylpropyl)-1-(2-phenylethyl)-2-pyrrolidinone (4.70 g, 19.2 mmol) and THF (80 mL) at -78° C. The solution is stirred at -78° C. for 45 minutes, and tert-butyl bromoacetate (3.4 mL, 23 mmol) is added. The solution is allowed to warm to 0° C. over 2 hours and is allowed to stir overnight at room temperature. After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (10% EtOAc/5% CH2Cl2 /hexane) to give 4.67 g (68%) of the title compound as a colorless oil. An analytical sample is crystallized from hexane (mp 50° C.).

Provenance & Evidence