1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 21866162, compound

HRID 857739Notes

Reaction equation

HRID 857739 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13]O.C1C=CC(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:29]([CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 21866194HCID 21866194, compound

Product 1

HCID 21866162HCID 21866162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2-pyrazin-2-ylphenyl)methanol (1.14 g, 6.13 mmol) in anhydrous THF (12.5 mL) at 0° C. was added DPPA (1.59 ml, 7.36 mmol) and DBU (1.01 mL, 6.75 mL). The resulting cloudy yellow mixture was allowed to warm to room temperature, and after 3.5 h was warmed to 80° C. for 3 h. The mixture was then cooled to room temperature and the THF was removed in vacuo. The residue was partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic extracts were washed successively with a 10% aqueous solution of citric acid, saturated aqueous NaHCO3 and brine. The organic solution was dried (anhydrous Na2SO4), filtered and concentrated to a yellow-brown oil. Silica gel chromatography (40% EtOAc-hexanes) afforded the title compound as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 8.82 (d, J=1.6 Hz, 1 H), 8.67 (dd, J=1.6, 2.4 Hz, 1 H), 8.59 (d, J=2.4 Hz, 1 H), 7.55–7.48 (m, 4 H), 4.60 (s, 2 H). LCMS (M+H): 212.1.

Workup

  1. temperatureafter 3.5 h was warmed to 80° C. for 3 h
  2. temperatureThe mixture was then cooled to room temperature
  3. customthe THF was removed in vacuo
  4. customThe residue was partitioned between EtOAc and H2O
  5. customThe layers were separated
  6. extractionthe aqueous layer was further extracted with EtOAc
  7. washThe combined organic extracts were washed successively with a 10% aqueous solution of citric acid, saturated aqueous NaHCO3 and brine
  8. dry with materialThe organic solution was dried (anhydrous Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated to a yellow-brown oil

Sources & evidence

ORD record
ord-eaf09d423b1e41c68249185a87f6dc7c
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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