Hydrogen Peroxide → 1,1-Dimethylethyl (2S)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5-dihydro-5-oxo-1H-pyrrole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of NaHMDS (35 mL, 35 mmol, 1.0M solution in THF) in THF (45 mL) at 0° C. was added DMPU (4.8 mL) and the reaction mixture was stirred 20 minutes. The reaction mixture was cooled to −78° C. and to it was added a solution of 4-2 (4.8 g, 14.6 mmol) in THF (20 mL) and the reaction was stirred an additional 30 minutes. At this time a solution of phenylselenenyl chloride (3.35 g, 17.5 mmol) in THF (15 mL) was added and the reaction was stirred at −78° C. for 2 h. The reaction quenched with saturated NH4Cl (200 mL) at −78° C. and the reaction mixture was warmed to ambient temperature. The reaction mixture was extracted with EtOAc (3×200 mL) and the combined organic phase was dried over magnesium sulfate and concentrated. The residue was resuspended in THF (100 mL) and cooled to 0° C. To the reaction mixture was added H2O2 (6.4 mL, 73 mmol, 35% solution in water). The reaction mixture was stirred 2 h and quenched with saturated NaHCO3 (200 mL). The reaction was extracted with EtOAc (3×200 mL) and the combined organic phase was dried over magnesium sulfate and concentrated. The residue was purified by normal phase silica gel chromatography (0 to 70% EtOAc in hexanes) to afford the product (4-3) as an off-white solid. ESI+ MS: [M-Boc+H]+ 228.3.

Provenance & Evidence