Aluminium lithium hydride → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

HRID 2036189Notes

Reaction equation

HRID 2036189 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:23])[NH:13][C:14]([C:17](=[O:22])N(OC)C)([CH3:16])[CH3:15])([CH3:10])([CH3:9])[CH3:8]>C(OCC)C>[C:7]([O:11][C:12](=[O:23])[NH:13][C:14]([CH3:16])([CH3:15])[CH:17]=[O:22])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 47451638HCID 47451638, compound2×

Product 1

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateYield 90.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (7.8 g) was added to a stirred solution of [1-(methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (compound L; 42.0 g) in dry diethyl ether (1.5 L) at −40° C. Then stirred at that temperature for about 5 min. Excess LiAlH4 was quenched with a solution of potassium hydrogen sulfate in water. The resulting mixture was partitioned between EtOAc and 3M aqueous HCl. The organic layer was washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo to afford (1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (compound M; 29 g) sufficiently pure for the next step.

Workup

  1. customExcess LiAlH4 was quenched with a solution of potassium hydrogen sulfate in water
  2. customThe resulting mixture was partitioned between EtOAc and 3M aqueous HCl
  3. washThe organic layer was washed with sat. aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68a226549e684db39af5124aaaeb6e70
Source dataset
uspto-grants-2013_11
Patent number
US08575174B2

Reaction notes

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