1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58188283, compound

HRID 1845132Notes

Reaction equation

HRID 1845132 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=1)O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(OP(OC2C=CC=CC=2)([N:28]=[N+:29]=[N-:30])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:28]([C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[N:14][CH:13]=1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 58188321HCID 58188321, compound

Product 1

HCID 58188283HCID 58188283, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of (R)-2-(tert-butyldimethylsilyloxy)-1-(6-methylpyridin-3-yl)ethanol (15.6 g, 0.055 mol) and diphenylphosphonic azide (62.8 mL, 0.292 mol) in toluene (200 mL) at 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (44.5 mL, 0.292 mol). The mixture was stirred at 0° C. for 30 minutes and then heated at 60° C. overnight. After cooling, the mixture was washed with water. The organic layer was dried and concentrated in vacuo. The residue was purified by flash chromatography (0-15% EtOAc/hexane) to afford a colorless oil.

Workup

  1. temperatureheated at 60° C. overnight
  2. temperatureAfter cooling
  3. washthe mixture was washed with water
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0-15% EtOAc/hexane)
  7. customto afford a colorless oil

Sources & evidence

ORD record
ord-dfa1d4c49a58410094cb8dd415c04c23
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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