Potassium bisulfate → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

HRID 660522Notes

Reaction equation

HRID 660522 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]([C:11](=[O:16])NCOC)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].OS([O-])(=O)=O.[K+]>CCOCC>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]([CH3:10])([CH3:9])[CH:11]=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 86632571HCID 86632571, compound

Product 1

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [1-(methoxymethyl-carbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.6 g, 7 mmol) in ether (30 mL) at −78° C. is added lithium aluminum hydride (9.8 mL of 1.0M in ether) dropwise. The mixture is warmed to 0° C. and stirred for 40 min. Aqueous KHSO4 (20 mL of 0.5M solution) is added and the mixture is extracted with ether. The organic solution is washed sequentially with 10% citric acid (2×), 5% NaHCO3 (2×) and brine. The solution is dried over magnesium sulfate and the solvent is removed under reduced pressure to afford the title compound.

Workup

  1. extractionthe mixture is extracted with ether
  2. washThe organic solution is washed sequentially with 10% citric acid (2×), 5% NaHCO3 (2×) and brine
  3. dry with materialThe solution is dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-cfd3a40f8f62467ea369ceed898d0206
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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