Oxonium, triethyl-, hexafluorophosphate(1-) (1:1) → tert-butyl 3-ethoxy-5,6-dihydropyrazine-1(2H)-carboxylate

HRID 340127Notes

Reaction equation

HRID 340127 reaction equation
F[P-](F)(F)(F)(F)F.C([O+:10]([CH2:13][CH3:14])[CH2:11][CH3:12])C.O=[C:16]1[NH:21]CC[N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1>>[CH2:13]([O:10][C:11]1[CH2:12][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][CH2:16][N:21]=1)[CH3:14]

Participants

3

Reactant 2

HCID 167684Oxonium, triethyl-, hexafluorophosphate(1-) (1:1)HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

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

Procedure

Triethyloxonium hexafluorophosphate (3.20 g, 28.0 mmol) was added to a solution of tert-butyl 3-oxopiperazine-1-carboxylate (2.54 g, 12.7 mmol) in CH2CL2 (31.7 mL) at 0° C., and the resulting solution was stirred at room temperature for 18 hours. The reaction mixture was washed with saturated NaHCO3, dried (Na2SO4), and concentrated to give tert-butyl 3-ethoxy-5,6-dihydropyrazine-1(2H)-carboxylate as an oil. LCMS (APCI+) M+H-t-Bu: 173 (40%); rt=3.14 minutes.

Workup

  1. washThe reaction mixture was washed with saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ce1daa0808c643259e3bdad29aea60df
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

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