反应详情

To a solution of 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate (3.60 g, 8.2 mmol) in THF (30 mL), was added a solution of nBu4NF (2.34 g, 9.0 mmol) in THF (20 mL). This mixture was stirred at room temperature over night. The solvent was removed under reduced pressure, and the residue was diluted with CH2Cl2 (50 mL), washed with water (15 mL×2), brine (15 mL×2), and dried over Na2SO4. The product 1,1-dimethylethyl {[3′-(hydroxymethyl)-4-methyl-3-biphenylyl]methyl}carbamate (1.5 g) was purified by flash column chomatography (PE:EA=4:1) (yield: 53%). 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 2.37 (s, 3H), 4.37 (d, J=5.6 Hz, 2H), 4.76 (m, 3H), 7.23-7.58 (m, 7H); 13C NMR (100 MHz, CDCl3) δ 18.6, 28.4, 42.9, 65.3, 79.5, 125.6, 125.7, 126.2, 126.8, 129.0, 130.9, 135.5, 138.9, 141.2, 141.4, 155.8; HPLC: retention time: 14.965 min; purity: 95.4%; MS m/z 327 (M+).

1. customThe solvent was removed under reduced pressure
2. additionthe residue was diluted with CH2Cl2 (50 mL)
3. washwashed with water (15 mL×2), brine (15 mL×2)
4. dry with materialdried over Na2SO4
5. customThe product 1,1-dimethylethyl {[3′-(hydroxymethyl)-4-methyl-3-biphenylyl]methyl}carbamate (1.5 g) was purified by flash column chomatography (PE:EA=4:1) (yield: 53%)