2,3-Dibromopropene → HCID 86631525, compound

HRID 911903Notes

Reaction equation

HRID 911903 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C([N-]C(C)C)(C)C.[Li+].[Br:22][C:23]([CH2:25]Br)=[CH2:24]>C1COCC1>[Br:22][C:23](=[CH2:24])[CH2:25][CH:6]1[CH2:5][CH2:4][N:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 105522,3-DibromopropeneHCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 2724682Lithium diisopropylamide

Product 1

HCID 86631525HCID 86631525, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a 250 mL round-bottom flask, tert-butyl 2-oxopyrrolidine-1-carboxylate (4.12 g, 22.2 mmol) was combined with 25 mL of THF and cooled to −78° C. Lithium diisopropylamide (1.5M in THF) (14.8 mL, 22.2 mmol) was added slowly and the mixture was agitated for 30 minutes. 2,3-Dibromopropene (2.72 mL, 22.2 mmol) was added and the mixture was agitated overnight and allowed to warm to ambient temperature. The reaction was then quenched with sodium bicarbonate solution and extracted twice with ether. The extracts were washed with brine and evaporated. The crude product was purified by column chromatography, eluting with 20% ethyl acetate/hexane, to provide the title compound (0.560 g, 8.3% yield).

Workup

  1. stirringthe mixture was agitated overnight
  2. temperatureto warm to ambient temperature
  3. customThe reaction was then quenched with sodium bicarbonate solution
  4. extractionextracted twice with ether
  5. washThe extracts were washed with brine
  6. customevaporated
  7. customThe crude product was purified by column chromatography
  8. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-20fe7e44781644c5b92da43089263cb6
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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