Ethyl Acrylate → Ethyl 3-(2-ethoxycarbonylethyl)amino-2,2-dimethylbutanoate

HRID 370290Notes

Reaction equation

HRID 370290 reaction equation
[NH2:1][CH:2]([CH3:11])[C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>C(O)C>[CH2:17]([O:16][C:12]([CH2:13][CH2:14][NH:1][CH:2]([CH3:11])[C:3]([CH3:9])([CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 23283845Ethyl 3-amino-2,2-dimethylbutanoate

Product 1

HCID 23283843Ethyl 3-(2-ethoxycarbonylethyl)amino-2,2-dimethylbutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In order to carry out this Michael addition, the ethyl 3-amino-2,2-dimethylbutanoate derivative 4 is dissolved with ethyl acrylate in a reaction medium which is inert under the reaction conditions chosen, preferably in a straight-chained or branched C1-4 -alkanol, most preferably ethanol, and heated, preferably to reflux temperature. After the reaction has taken place the solvent is eliminated in vacuo and the resulting ethyl 3-(2-ethoxycarbonylethyl)amino-2,2-dimethylbutanoate 5 is isolated.

Workup

  1. additionthis Michael addition
  2. customis inert under the reaction conditions
  3. temperaturepreferably to reflux temperature

Sources & evidence

ORD record
ord-e36029eadf88402d84e9ce1159a782be
Source dataset
uspto-grants-2000_10
Patent number
US06140502

Reaction notes

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