Ethyl bromoacetate → Ethyl 4,5-dioxo-1-phenyl-3-pyrrolidineacetate

HRID 1034249Notes

Reaction equation

HRID 1034249 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][C:9](=[O:12])[C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1COCC1>[O:12]=[C:9]1[C:8](=[O:13])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11][CH:10]1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 190235711-Phenylpyrrolidine-2,3-dione

Product 1

HCID 57059855Ethyl 4,5-dioxo-1-phenyl-3-pyrrolidineacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the product of Example 61 in THF is added to a solution of lithium di-iso-propylamide (LDA) in THF at -78° C. After 2 h at -78° C. a solution of ethyl bromoacetate is added and the reaction is allowed to warm to room temperature. After an aqueous workup the crude product is chromatographed on silica gel to give the title compound.

Workup

  1. customAfter an aqueous workup the crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-9614d5b86732459194f1a2cfec8b8256
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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