Water → HCID 10967168, compound

HRID 2296655Notes

Reaction equation

HRID 2296655 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]=[C:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].O>CC(O)=O.[Pd].[H][H]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 962WaterHCID 11128927HCID 11128927, compound

Product 1

HCID 10967168HCID 10967168, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Ethyl 1-tert-butoxycarbonyl-1,4,5,6-tetrahydropyrazinecarboxylate (60 g) was dissolved in AcOH (400 ml), and the solution was subjected to catalytic reduction using 10% palladium on carbon (12 g)-H2O (30 ml), in hydrogen at 3 atm for 4 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in AcOEt (1000 ml), and the organic layer was washed with saturated aqueous NaHCO3 solution by stirring carefully to avoid foaming. The organic layer was further washed with saturated brine, and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure to give 59.2 g of ethyl 1-tert-butoxycarbonyl-2-piperazinecarboxylate as an oil (yield 97.9%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in AcOEt (1000 ml)
  4. washthe organic layer was washed with saturated aqueous NaHCO3 solution
  5. washThe organic layer was further washed with saturated brine
  6. dry with materialdried over anhydrous MgSO4
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-843406f4301f4fc4938a07e230d5531f
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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