Water → 3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-

Participants

Reaction Conditions

Reaction Steps

Add dropwise over 2 hours a solution of pyridine sulfur trioxide (390 g, 2452.83 mmol) in dimethylsulfoxide (1600 mL) to a 6° C. maintained solution of (S)-4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (350 g, 1515.15 mmol) in diisopropylethylamine (1225 mL) with a dimethylsulfide trap. Over 30 minutes add water (1050 mL) keeping temperature below 15° C. Stir at 15° C. for 1.5 hours under a stream of nitrogen. Extract with ethyl acetate (5 L), wash with 5%-aqueous citric acid (2×1.5 L), saturated aqueous sodium chloride (2×1.5 L), dry (magnesium sulfate), filter, and concentrate to give the desired compound which is used in the next reaction without further purification (365 g).

Provenance & Evidence