反应详情

To a 0° C. solution of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-carbamic acid benzyl ester (18 g, 48.5 mmol) in DMF (100 mL) is added sodium hydride (60% dispersion in oil, 2.3 g, 58 mmol) portionwise. The reaction mixture is stirred at room temperature for 30 minutes, followed by the addition of iodomethane (8.2 g, 58 mmol). The mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure to give a residue, which is partitioned between EtOAc (100 mL) and water (100 mL). The organic phase is washed with brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to give [4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-carbamic acid benzyl ester as oil (14.0 g, 75%). LC-ES/MS: 386.0 (M+1).

1. stirringThe mixture is stirred at room temperature overnight
2. customThe solvent is removed under reduced pressure
3. customto give a residue, which
4. customis partitioned between EtOAc (100 mL) and water (100 mL)
5. washThe organic phase is washed with brine (100 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure to a residue
9. customThe residue is purified by flash chromatography