Sodium Thiosulfate → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (10 g) in acetonitrile (133 ml) was added Dess-Martin periodinane (13.53 g) under ice-cooling, and the mixture was stirred under ice-cooling for 3 hr. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate and aqueous saturated sodium thiosulfate solution at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (8.3 g).

Provenance & Evidence