Ammonium Chloride → 3-{5-[(5R)-5-(Hydroxylmethyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-[(1S)-2-methoxy-1-methylethoxy]phenol

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Reaction Conditions

Reaction Steps

(5R)-2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrol-2-yl)-5{[(triisopropylsilyl)oxy]methyl}-4,5-dihydro-1,3-oxazole (9.69 g, 14.7 mmol) synthesized in Example (1250 was dissolved in tetrahydrofuran (150 mL), and tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 30.0 mL, 30 mmol) was added dropwise at 0° C., followed by stirring at 0° C. for 30 minutes. A saturated aqueous ammonium chloride solution (200 mL) was added, and extraction was carried out with ethyl acetate (200 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: methanol/methylene chloride=3%-7%) to afford the desired compound (6.50 g, yield ˜100%) as a pale yellow solid.

Provenance & Evidence