Methyl iodide → [4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-carbamic acid benzyl ester

HRID 424805Notes

Reaction equation

HRID 424805 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:13][C:12]=1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:30]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:26])[N:10]([C:11]1[CH:16]=[CH:15][C:14]([O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])=[CH:13][C:12]=1[CH3:25])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66704185[4-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-carbamic acid benzyl ester

Product 1

HCID 66704094[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-carbamic acid benzyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-31450131444a48b78731389868ffd237
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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