Homoallyl bromide → Tert-butyl 4-but-3-enyl-3-oxopiperazine-1-carboxylate

HRID 227478Notes

Reaction equation

HRID 227478 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].Br[CH2:18][CH2:19][CH:20]=[CH2:21]>CN(C=O)C.C1COCC1>[CH2:21]([N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][C:2]1=[O:1])[CH2:20][CH:19]=[CH2:18]

Participants

6

Reactant 3

HCID 21241Homoallyl bromideHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 57445033Tert-butyl 4-but-3-enyl-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-oxopiperazine-1-carboxylate (0.500 mg, 2.50 mmol) in 10 mL of DMF at 0° C. was added NaH as a 60% dispersion in mineral oil (2.62 mmol), and the reaction was stirred for 45 minutes. 4-Bromo-1-butene was added (0.280 mL, 2.75 mmol) dropwise as a solution in 1 mL of THF. The solution was stirred overnight, allowing it to warm to room temperature. The reaction was partitioned between EtOAc and saturated NaHCO3 solution. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to give the titled compound. Proton NMR for the product was consistent with the titled compound. ESI+MS: 255.1 [M+H]+.

Workup

  1. stirringThe solution was stirred overnight
  2. customThe reaction was partitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3fd5fa11813499d9043c36d7d51ceb0
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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