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

HRID 2111261Notes

Reaction equation

HRID 2111261 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[C:5]([C:8]#[N:9])([CH3:7])[CH3:6])C.[H][H]>[Ni].CO>[CH3:1][O:3][C:4](=[O:10])[C:5]([CH3:7])([CH3:6])[CH2:8][NH2:9]

Participants

5

Reactant 2

HCID 344887Ethyl 2-Cyano-2-methylpropionateHCID 178418361HCID 178418361, compound

Product 1

HCID 13285789Methyl 3-amino-2,2-dimethylpropanoateYield 94.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10 g of Raney-nickel 2800 was transferred to a 500 mL hydrogenation vessel and washed three times with 40 mL of methanol. Then, 180 mL of methanol and 25.0 g (0.177 mole) of 2-cyano-2-methylpropanoic acid ethyl ester was added and the mixture agitated on a Paar hydrogenator under a 50 psi atmosphere of hydrogen for 24 hours. The mixture was filtered through Celite, washing the filter pad with methanol, and then concentrated under reduced pressure to give 21.98 g of 3-amino-2,2-dimethyl-propanoic acid methyl ester, which was used without further purification.

Workup

  1. customwas transferred to a 500 mL hydrogenation vessel
  2. washwashed three times with 40 mL of methanol
  3. filtrationThe mixture was filtered through Celite
  4. washwashing the filter pad with methanol
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f8164d0778c4cd892e261f6c63b34ec
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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