Diethyl Oxalate → ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate

HRID 1697892Notes

Reaction equation

HRID 1697892 reaction equation
[O-]CC.[Na+].[CH2:5]([O:7][C:8](=[O:19])[CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:6].[C:20](OCC)(=[O:26])[C:21](OCC)=[O:22]>C(O)C>[CH2:12]([N:11]1[C:21](=[O:22])[C:20](=[O:26])[CH:9]([C:8]([O:7][CH2:5][CH3:6])=[O:19])[CH2:10]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 90196N-(Phenylmethyl)-beta-alanine ethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 219271ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21% Sodium ethoxide in ethanol (21:79, sodium ethoxide:ethanol, 56.0 mL) was added dropwise to a mixture of ethyl-beta-benzylaminopropionate (22.178 g, 0.10700 mol) and diethyl oxalate (15.0 mL, 0.110 mol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and then water (about 200 mL) was added. The mixture was stirred for 5 min and then 1M HCl was added until pH 1. The mixture was vacuum filtered. The solids were collected and dried in vacuo overnight, and then crystallized from ethanol to give the desired product (20.946 g, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (about 200 mL) was added
  3. stirringThe mixture was stirred for 5 min
  4. addition1M HCl was added until pH 1
  5. filtrationfiltered
  6. customThe solids were collected
  7. customdried in vacuo overnight
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-ba61e4ada8514e93918d2104cafc8147
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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