Methyl Methacrylate → Methyl 2-methyl-3-[(phenylmethyl)amino]propanoate

HRID 1485418Notes

Reaction equation

HRID 1485418 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:14][CH3:15])(=[O:13])[C:10]([CH3:12])=[CH2:11]>CO>[CH2:1]([NH:8][CH2:11][CH:10]([CH3:12])[C:9]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6658Methyl MethacrylateHCID 7504Benzylamine

Product 1

HCID 97781Methyl 2-methyl-3-[(phenylmethyl)amino]propanoateYield 57.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzylamine (10.7 g, 100 mmol) in methanol (100 mL) was added methyl methacrylate (10 g, 100 mmol). The reaction solution was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give methyl 3-(benzylamino)-2-methylpropanoate as a light yellow oil (12 g, 57%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-53f705ab13db4d52b1223e99ce7b3f5e
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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