Aluminium lithium hydride → 2-Amino-2-(3,4-difluorophenyl)ethanol

HRID 2087147Notes

Reaction equation

HRID 2087147 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH:10]([NH2:19])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1>C1COCC1>[NH2:19][CH:10]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1)[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22049608Methyl 2-aMino-2-(3,4-difluorophenyl)acetate

Product 1

HCID 220488782-Amino-2-(3,4-difluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a well-stirred suspension of LiAlH4 (4.7 g, 0.125 mol) in THF (120 mL) in a 3-necked round bottom flask fitted with a condenser and a dropping funnel, was added a solution of amino-(3,4-difluorophenyl)-acetic acid methyl ester (10.0 g, 0.05 mol) in THF (100 mL) dropwise at 0° C. The resulting greenish brown suspension was heated at reflux temperature for 2 h. The reaction mixture was cooled to 0° C. and then carefully quenched sequentially with 5 mL of water, 5 mL of 3N NaOH followed by 15 mL of water. The resulting suspension was filtered through a fritted glass funnel. To the filter cake was added 100 mL Et2O and the suspension was heated at reflux temperature for 20 min. The suspension was filtered and the combined filtrates were dried over MgSO4, filtered and the solvent was removed in vacuo. 2-Amino-2-(3,4-difluorophenyl)-ethanol was obtained as a yellow glassy syrup which was used in the next step without further purification.

Workup

  1. customfitted with a condenser and a dropping funnel
  2. temperatureThe resulting greenish brown suspension was heated
  3. temperatureat reflux temperature for 2 h
  4. customcarefully quenched sequentially with 5 mL of water, 5 mL of 3N NaOH
  5. filtrationThe resulting suspension was filtered through a fritted glass funnel
  6. additionTo the filter cake was added 100 mL Et2O
  7. temperaturethe suspension was heated
  8. temperatureat reflux temperature for 20 min
  9. filtrationThe suspension was filtered
  10. dry with materialthe combined filtrates were dried over MgSO4
  11. filtrationfiltered
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aff133bb55af4d20a3c4be9ec7ef3944
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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