Dichloromethane → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To an ice cold solution of (2R,4R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (7.48 g, 13.0 mmol) in 20:1 dichloromethane:water (130 mL) add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (4.71 g, 20.74 mmol). Stir 4 h in an ice bath and wash with saturated aqueous sodium bicarbonate (3×300 mL), saturated aqueous sodium chloride, dry magnesium sulfate and purify on silica gel with dichloromethane/ethyl acetate mixtures to give the title compound as a foam (5.288 g, 89%).

Provenance & Evidence