Ethyl Acetate → tert-Butyl [2-(2-hydroxyethyl)phenyl]carbamate

HRID 1356427Notes

Reaction equation

HRID 1356427 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](CC(O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:25](OCC)(=[O:27])[CH3:26]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:26][CH2:25][OH:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10752353tert-Butyl [2-(2-hydroxyethyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(t-butoxycarbonylamino)-benzeneacetic acid (2.9 g, 11.4 mmoles) is dissolved in 10 ml of anhydrous THF at 0° C. and added to a suspension of LiAlH4 (0.52 g, 13.6 mmoles) in 30 ml of THF. The reaction mixture is agitated at ambient temperature for 1.5 hours. 50 ml of ethyl acetate then 20 ml of 2N soda are added to the medium. The expected product is extracted from the organic phase, which is then washed with 3 times 15 ml of water. The organic phase is dried and the solvent evaporated off under reduced pressure. Then the reaction product is purified on silica gel in a dichloromethane/methanol mixture (95/5). 1.1 g (40%) is thus obtained in the form of a colourless oil.

Workup

  1. extractionThe expected product is extracted from the organic phase, which
  2. washis then washed with 3 times 15 ml of water
  3. customThe organic phase is dried
  4. customthe solvent evaporated off under reduced pressure
  5. customThen the reaction product is purified on silica gel in a dichloromethane/methanol mixture (95/5)
  6. custom1.1 g (40%) is thus obtained in the form of a colourless oil

Sources & evidence

ORD record
ord-15357d38ef544304bc18db62fd718b43
Source dataset
uspto-grants-2003_07
Patent number
US06586454B2

Reaction notes

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