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

HRID 2404125Notes

Reaction equation

HRID 2404125 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-dc5776a6edc6457dba87ad4b1a13420c
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

Loading…