Tetrabutylammonium Fluoride → 1,1-Dimethylethyl {[3'-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate

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Reaction Steps

To a solution of 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate (1.5 g, 3.28 mmol) in THF (20 mL), the solution of nBu4NF (0.94 g, 3.61 mmol) in THF (10 mL) was added, and then the mixture was stirred at room temperature over night. After the solvent was removed under reduced pressure, the residue was diluted with EtOAc (30 mL). The organic layer was washed with water (10 mL×2), brine (10 mL×2), and dried over Na2SO4. The product 1,1-dimethylethyl {[3′-(hydroxymethyl)-5-(methyloxy)-3-biphenylyl]methyl}carbamate (0.9 g) was purified by flash column chromatography (PE:EA=3:1). (Yield: 80%). 1H NMR (400 MHz, CDCl3): δ 1.47 (s, 9 H), 3.86 (s, 3 H), 4.35 (d, J=7.6 Hz, 2 H), 4.76 (s, 2 H), 4.89 (s, 1 H), 6.83 (s, 1 H), 7.02 (s, 1 H), 7.09 (s, 1 H), 7.34-7.58 (m, 4H); 13C NMR (100 MHz, CDCl3): δ 28.4, 44.7, 55.4, 65.2, 79.6, 111.9, 118.7, 125.8, 126.1, 126.4, 129.0, 140.9, 141.2, 141.5, 142.8, 156.0, 160.3. HPLC: retention time: 11.558 min; purity: 98.7%; MS: m/z 343 (M+).

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