1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 21471618, compound

HRID 2294935Notes

Reaction equation

HRID 2294935 reaction equation
O[CH:2]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)[CH3:3].C1(P([N:24]=[N+:25]=[N-:26])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:24]([CH:2]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)[CH3:3])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 5730131-Pyrazin-2-yl-ethanol

Product 1

HCID 21471618HCID 21471618, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-(1-hydroxyethyl)pyrazine (0.859 g) and diphenylphosphoryl azide (2.48 g) in dry toluene (12 mL) at 0° C., under argon, was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.35 mL) dropwise. The resulting mixture was allowed to warm slowly to room temperature and stirred for 22 h then quenched with water (8 mL). The organic layer was removed and the aqueous phase extracted with 10 mL ethyl acetate. The combined extracts were concentrated, and the crude product was purified by flash column chromatography, eluting with hexane; 25% ethyl acetate to give 2-(1-azidoethyl)pyrazine (0.88 g) as a colorless oil.

Workup

  1. customthen quenched with water (8 mL)
  2. customThe organic layer was removed
  3. extractionthe aqueous phase extracted with 10 mL ethyl acetate
  4. concentrationThe combined extracts were concentrated
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with hexane

Sources & evidence

ORD record
ord-f65dd98545574dab893f2736c4c5c27a
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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