Water → HCID 19434882, compound

Participants

Reaction Steps

4.64 g (10.9 mmol) of the above ethyl 4-azido-3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)benzoate was dissolved in 100 mL of methanol, 2.90 g (76.7 mmol) of sodium borohydride was added in several portions under ice-cooling, 10 mL of water was further added and the mixture was stirred at room temperature for 4.5 hours. The solvent was distilled off under reduced pressure, water was added and the mixture was extracted once with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give 4.09 g of ethyl 4-amino-3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)benzoate (yield: 94%).

Provenance & Evidence