Ethyl 2-Cyano-2-methylpropionate → Ethyl 3-amino-2,2-dimethylpropanoate

HRID 1481000Notes

Reaction equation

HRID 1481000 reaction equation
[C:1]([C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]>CCO.[Ni]>[NH2:2][CH2:1][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 344887Ethyl 2-Cyano-2-methylpropionate

Product 1

HCID 421529Ethyl 3-amino-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a slurry of Raney-Ni (1.6 g, 50% in H2O, rinsed 3 times with EtOH before use) in EtOH (78 mL) was added ethyl 2-cyano-2-methylpropanoate (5 g, 35 mmol). The resulting mixture was stirred under a hydrogen atmosphere at room temperature for 20 hours. The liquid was then carefully decanted into another flask and the metal was washed twice with EtOH. The combined EtOH solution was concentrated in vacuo to give the title compound in 4.5 g, which was used in the subsequent step without further purification. 1H NMR (CDCl3, 200 MHz): δ=4.13 (q, 2H, J=7.0 Hz), 2.74 (s, 2H), 1.26 (t, 3H, J=7.0 Hz), 1.17 (s, 6H).

Workup

  1. customThe liquid was then carefully decanted into another flask
  2. washthe metal was washed twice with EtOH
  3. concentrationThe combined EtOH solution was concentrated in vacuo

Sources & evidence

ORD record
ord-79d12438714144b8b72ad3799cb7b29d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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