Acrylonitrile → Methyl 3-(2-cyano-ethylamino)-2,2-dimethylpropanoate

HRID 550596Notes

Reaction equation

HRID 550596 reaction equation
[NH2:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[C:10](#[N:13])[CH:11]=[CH2:12]>CO>[C:10]([CH2:11][CH2:12][NH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])#[N:13]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 13285789Methyl 3-amino-2,2-dimethylpropanoate

Product 1

HCID 86626329Methyl 3-(2-cyano-ethylamino)-2,2-dimethylpropanoateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-amino-2,2-dimethylpropanoate (1.0 g, 7.63 mmol) and acrylonitrile (2 eq., 1 mL, 15.26 mmol) in methanol (50 mL) was stirred at room temperature for about 18 hours. After evaporation of the solvent, the residue was purified by flash chromatography on silica gel, using cyclohexane-ethyl acetate 1:1 as eluant, to give the title compound as colourless oil (0.7 g, 70% yield).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5776beb77a7944079cfebf5714ed6082
Source dataset
uspto-grants-2011_05
Patent number
US07947686B2

Reaction notes

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