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

HRID 713905Notes

Reaction equation

HRID 713905 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH2:8]([NH:15][CH2:3][CH:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6658Methyl MethacrylateHCID 7504Benzylamine

Product 1

HCID 97781Methyl 2-methyl-3-[(phenylmethyl)amino]propanoateYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl methacrylate (7 mL, 0.067 mol, 1.0 equiv), benzylamine (6 mL, 0.055 mol, 0.8 equiv) in methanol (5 ml) was stirred at 70° C. for 2 days. After evaporation of the volatiles, the crude product was purified by flash chromatography (DCM:MeOH=20:1) to give compound methyl 3-(benzylamino)-2-methylpropanoate 9 g, yield: 65%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.32-7.24 (m, 5H), 3.79 (s, 2H), 3.68 (s, 3H), 2.88-2.85 (m, 1H), 2.71-2.63 (m, 2H), 1.16 (d, 3H).

Workup

  1. customAfter evaporation of the volatiles
  2. customthe crude product was purified by flash chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-92dc398330c441e0868666f7cd978656
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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