Water → tert-butyl [(2R)-2-methoxypropyl]methylcarbamate

HRID 1910399Notes

Reaction equation

HRID 1910399 reaction equation
[CH3:1][O:2][C@H:3]([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Na+].[CH3:16]I.O>CN(C=O)C>[CH3:1][O:2][C@H:3]([CH3:13])[CH2:4][N:5]([CH3:16])[C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86641515tert-butyl [(2R)-2-methoxypropyl]carbamate

Product 1

HCID 86641516tert-butyl [(2R)-2-methoxypropyl]methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl [(2R)-2-methoxypropyl]carbamate (2.72 g) in DMF (41 ml) was added NaH (862 mg; 60% oil suspension) under nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. MeI (1.79 ml) was added to the mixture, and the whole was stirred for 3 hours at the same temperature. Water was added, and the whole was extracted with EtOAc and the extract was washed with water and brine and dried over MgSO4. Concentration under reduced pressure gave a residual oil, which was purified with silica gel column eluting with EtOAc:n-hexane=1:5 to give tert-butyl [(2R)-2-methoxypropyl]methylcarbamate (1.94 g).

Workup

  1. stirringthe whole was stirred for 3 hours at the same temperature
  2. extractionthe whole was extracted with EtOAc
  3. washthe extract was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration under reduced pressure
  6. customgave a residual oil, which
  7. customwas purified with silica gel column
  8. washeluting with EtOAc

Sources & evidence

ORD record
ord-1fa1070780ac4e75b16000b8d8d4e67d
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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