Dimethyl N-(1-methylethyl)-glutamate → methyl (2S)-5-oxo-1-(propan-2-yl)pyrrolidine-2-carboxylate

HRID 2238476Notes

Reaction equation

HRID 2238476 reaction equation
[CH3:1][CH:2]([NH:4][C@H:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH2:7][C:8](OC)=[O:9])[CH3:3]>CO>[CH3:1][CH:2]([N:4]1[C:8](=[O:9])[CH2:7][CH2:6][C@H:5]1[C:12]([O:14][CH3:15])=[O:13])[CH3:3]

Participants

3

Reactant 1

HCID 12968093Dimethyl N-(1-methylethyl)-glutamate

Product 1

HCID 67461795methyl (2S)-5-oxo-1-(propan-2-yl)pyrrolidine-2-carboxylateYield 89.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

Dimethyl N-(1-methylethyl)-glutamate (0.200 g) was dissolved in methanol and heated in a sealed tube in a microwave reactor at 140° C. for 20 minutes. Thin-layer chromatography indicated that the starting material remained intact so the solvent was evaporated and replaced with toluene. The mixture was heated at reflux temperature for ˜3 hrs and then evaporated to give methyl 1-(1-methylethyl)-5-oxo-prolinate (0.152 g) as a light yellow oil which was used in the subsequent step without further purification.

Workup

  1. customwas evaporated
  2. temperatureThe mixture was heated
  3. temperatureat reflux temperature for ˜3 hrs
  4. customevaporated

Sources & evidence

ORD record
ord-e7717f8ac0cb40fb8d93e19772cfe985
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

Loading…