1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22929666, compound

HRID 1296010Notes

Reaction equation

HRID 1296010 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[CH:29]1([C:32]2[N:37]=[CH:36][C:35]([CH2:38]O)=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:29]1([C:32]2[N:37]=[CH:36][C:35]([CH2:38][N:15]=[N+:16]=[N-:17])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 22929956HCID 22929956, compound

Product 1

HCID 22929666HCID 22929666, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diphenylphosphoryl azide (0.49 ml, 2.3 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.34 ml, 2.3 mmol) were added dropwise in that order at room temperature to a solution of (6-cyclopropyl-3-pyridyl)methanol (283 mg, 1.90 mmol) in toluene (4 ml) and the mixture was stirred for 3 hours. After confirming completion of the reaction by thin layer chromatography, it was diluted with ethyl acetate and washed with water and brine. Drying was performed with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (330 mg, quant.) as a colorless oil.

Workup

  1. customcompletion of the reaction by thin layer chromatography, it
  2. washwashed with water and brine
  3. customDrying
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bf210aa71b0e498e966bdd1598e92494
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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