Sodium Bicarbonate → tert-butyl 3-ethoxy-5,6-dihydropyrazine-1(2H)-carboxylate

HRID 576687Notes

Reaction equation

HRID 576687 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.F[B-](F)(F)F.[CH2:20]([O+](CC)CC)[CH3:21].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:20]([O:1][C:2]1[CH2:3][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH2:6][N:7]=1)[CH3:21]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 67439401tert-butyl 3-ethoxy-5,6-dihydropyrazine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-oxopiperazine-1-carboxylate (1 g, 5 mmol) in DCM (15 mL) was added triethyloxonium tetrafluoroborate (2.9 g, 15 mmol). Stirred for 2 h and neutralized with sat. aq NaHCO3. Layers separated and aqueous layer extracted with DCM. Combined organic layers dried over Na2SO4, filtered, and concentrated to give the title compound, which was used directly without further purification.

Workup

  1. customLayers separated
  2. extractionaqueous layer extracted with DCM
  3. dry with materialCombined organic layers dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-35496499ef744be4bf4ed12ae41b64c8
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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