Methyl iodide → (2S,3S)-3-tert-butyldimethylsilanyloxy-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 4A (898 mg, 2.50 mmol) in THF (10 mL) at −78° C. under nitrogen was added a 1.8 M solution of LDA (3.50 mL, 6.25 mmol) and the reaction was stirred at −78° C. for 1 h. Iodomethane (1.56 mL, 25.0 mmol) was added, and the mixture was stirred at −78° C. for 4 h. The reaction was quenched by adding EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, then dried over MgSO4, filtered and concentrated. Purification via silica gel chromatography (0-15% EtOAc in hexane) provided compound 4B (276 mg).

Provenance & Evidence