Methanol → 3-(4-Aminomethyl-phenyl)-propionic acid tert-butyl ester

HRID 64415Notes

Reaction equation

HRID 64415 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].CO.C1COCC1>[C].[Pd].C(O)(=O)C>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11287649Tert-butyl 3-(4-cyanophenyl)prop-2-enoate

Product 1

HCID 534077053-(4-Aminomethyl-phenyl)-propionic acid tert-butyl esterYield 77.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To 223 mg of tert-butyl (2E)-3-(4-cyanophenyl)acrylate were added 12 mL of methanol, 5 ml of THF, 1 ml of an acetic acid solution, and 90 mg of 10% palladium-carbon in this order, followed by stirring for 3 hours under hydrogen at 3 atm. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. To the residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 177 mg of tert-butyl 3-[4-(aminomethyl)phenyl]propanoate.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  4. customa layer separation operation
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aa6c850cff324b2188b72ea3469c462e
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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