Water → [2-(4-Fluoro-3-methoxyphenyl)ethyl]methylcarbamic acid t-butyl ester

HRID 1351262Notes

Reaction equation

HRID 1351262 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([O:17][CH3:18])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([O:17][CH3:18])[CH:11]=1)[CH3:22])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69415384[2-(4-Fluoro-3-methoxyphenyl)ethyl]carbamic acid t-butyl ester

Product 1

HCID 69413197[2-(4-Fluoro-3-methoxyphenyl)ethyl]methylcarbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(4-fluoro-3-methoxyphenyl)ethyl]carbamic acid t-butyl ester (795 mg) in N,N-dimethylformamide (6 mL) was added 60% sodium hydride (154 mg) at room temperature. After stirring for 1 hour, methyl iodide (0.55 mL) was added dropwise and the solution was stirred for 14 hours. Water was added cautiously by small amounts, and after extraction with ethyl acetate, the solution was washed with water and saturated sodium chloride water. The residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (506 mg) was obtained as a colorless oily matter.

Workup

  1. stirringthe solution was stirred for 14 hours
  2. extractionafter extraction with ethyl acetate
  3. washthe solution was washed with water and saturated sodium chloride water
  4. customThe residue that was obtained
  5. customupon removing the solvent
  6. customby evaporation
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8b65e8c0eb1846bb9841a414984ada84
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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