tert-Butyl(2E)-3-(3-amino-4-cyanophenyl)-2-methylacrylate → Tert-butyl 3-(3-amino-4-cyanophenyl)-2-methylpropanoate

HRID 1476129Notes

Reaction equation

HRID 1476129 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[CH3:19])/[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 1

HCID 67215496tert-Butyl(2E)-3-(3-amino-4-cyanophenyl)-2-methylacrylate

Product 1

HCID 58288219Tert-butyl 3-(3-amino-4-cyanophenyl)-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1370 mg (5.3 mmol) of tert-butyl (2E)-3-(3-amino-4-cyanophenyl)-2-methylacrylate were dissolved in 30 ml of ethyl acetate, 282 mg of palladium on carbon (10%) were added and the mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure for three days. The reaction mixture was then filtered off through celite, the filter residue was washed with ethyl acetate and the combined filtrate was concentrated. The crude product was purified by preparative HPLC (mobile phase acetonitrile/water). This gave 870 mg of the title compound (63% of theory).

Workup

  1. filtrationThe reaction mixture was then filtered off through celite
  2. washthe filter residue was washed with ethyl acetate
  3. concentrationthe combined filtrate was concentrated
  4. customThe crude product was purified by preparative HPLC (mobile phase acetonitrile/water)

Sources & evidence

ORD record
ord-1b2136fb0974426cb806f675ebc011db
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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