Sodium periodate → HCID 59456436, compound

Participants

Reaction Steps

A solution of 1.07 g (5.0 mmol) of sodium periodate and 0.338 g (0.15 mmol) of ruthenium(III) chloride hydrate in 12.5 ml of water was added to 0.44 g (1 mmol) of 1-tert-butyl 2-methyl 4-[2-(toluene-4-sulfonyloxy)ethoxy]pyrrolidine-1,2-dicarboxylate in 20 ml of dichloromethane. The mixture was left at room temperature for three days with vigorous stirring. Subsequently, the phases were separated, the aqueous phase was extracted twice with ethyl acetate (20 ml) and the combined organic phases were stirred with 5 ml of isopropanol for 30 min. The mixture was dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The crude product was purified by column chromatography (silica gel, hexane/ethyl acetate). 0.11 g (24%) of 1-tert-butyl 2-methyl 5-oxo-4-[2-(toluene-4-sulfonyloxy)ethoxy]pyrrolidine-1,2-dicarboxylate (23) was obtained as a colorless oil.

Provenance & Evidence