Methyl iodide → tert-Butyl alpha-Methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

Participants

Reaction Conditions

Reaction Steps

LDA (1.5 mL, 3.0 mmol, 2.0M in heptane/THF/ethylbenzene) is added to a solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (967 mg, 2.69 mmol) and THF (11.0 mL) at -78° C. The solution is stirred at -78° C. for 30 minutes and then iodomethane (0.19 mL, 3.1 mmol) is added. The solution is stirred at -78° C. for 2 hours and then allowed to slowly warm to room temperature overnight. Aqueous workup (EtOAc, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc) gives 791 mg (79%) of the title compound as an oil.

Provenance & Evidence