Acetic Acid → 2-(3-Aminomethyl-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1242375Notes

Reaction equation

HRID 1242375 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C(O)(=O)C>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 582440942-(3-Cyano-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 580095732-(3-Aminomethyl-phenoxy)-2-methyl-propionic acid ethyl esterYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8.56 g (36.7 mmol) of 2-(3-cyano-phenoxy)-2-methyl-propionic acid ethyl ester was dissolved in 65 ml ethanol; then, 6.5 ml acetic acid was added, followed by 0.9 g Pd—C (10%) and the reaction mixture was hydrogenated under 1 atm of H2-pressure during 5 hours. Then, it was filtered (Celite), the filter cake was washed twice with ethanol and the solvents were evaporated. The residue was partitioned between crashed ice/1N NaOH/EtOAc and extracted twice with EtOAc; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, MeCl2/MeOH) to give 7.71 g of the title compound as colorless oil.

Workup

  1. filtrationThen, it was filtered (Celite)
  2. washthe filter cake was washed twice with ethanol
  3. customthe solvents were evaporated
  4. customThe residue was partitioned
  5. extractionextracted twice with EtOAc
  6. washthe organic phases were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe crude product was purified by flash chromatography (SiO2, MeCl2/MeOH)

Sources & evidence

ORD record
ord-165d737fb0b0483aa05802e9e98f53b1
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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