Ethyl bromoacetate → HCID 22277832, compound

HRID 1064019Notes

Reaction equation

HRID 1064019 reaction equation
[H-].[Na+].[CH2:3]([CH:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH2:3]([CH:10]1[CH2:14][CH2:13][N:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]1=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 102412993-benzylpyrrolidin-2-one

Product 1

HCID 22277832HCID 22277832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (50%, 0.214 g, 4.5 mmol) was added to a solution of 3-benzyl-2-pyrrolidinone (Synthesis, 1996, 8, 941-948; 0.68 g, 3.9 mmol) in THF (15 ml). The solution was stirred at room temperature for 30 minutes. Ethyl bromoacetate (0.48 ml, 4.3 mmol) was added and the mixture stirred for 12 hours. The solvent was removed in vacuo and the residue purified by chromatography eluting with 50% EtOAc in hexane to give the product as a light yellow oil. NMR (90 MHz, CDCl3) 7.2 (m, 5H), 4.2 (m, 3H), 3.25 (m, 1H), 2.75 (m, 2H), 2.3-1.6 (m, 4H), 1.3 (t, 3H).

Workup

  1. stirringthe mixture stirred for 12 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by chromatography
  4. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-dd261a3402c7425aa8b995c0d996eb3e
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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