Tetrabutylammonium Fluoride → 3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenol

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Reaction Steps

(5S)-2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-4,5-dihydro-1,3-oxazole (29.5 g, 60.7 mmol) synthesized in Example (116c) was dissolved in tetrahydrofuran (400 mL), and tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 66 mL, 66 mmol) was added, followed by stirring for 1 hour under nitrogen atmosphere. The solvent was distilled off under reduced pressure, water (400 mL) was added to the residue, and extraction was carried out twice with ethyl acetate (400 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-50%) to afford the desired compound (16.7 g, yield 83%) as a white solid.

Provenance & Evidence