Boron tribromide → 3-[(1S)-2-Hydroxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol

Participants

Reaction Steps

3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol (60 mg, 0.18 mmol) synthesized in Example (116d) was dissolved in methylene chloride (4 mL), and boron tribromide (1.0 mol/L methylene chloride solution, 0.38 mL, 0.38 mmol) was added at −78° C. under nitrogen atmosphere. Subsequently, the temperature was brought back to room temperature, followed by stirring for 1 hour. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: hexane/ethyl acetate=50%-70%) to afford the desired compound (41 mg, yield 72%) as a white solid.

Provenance & Evidence