1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylate

HRID 332683Notes

Reaction equation

HRID 332683 reaction equation
O[CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]([O:19][CH3:20])=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C1(P([N:44]=[N+:45]=[N-:46])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:44]([CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]([O:19][CH3:20])=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)=[N+:45]=[N-:46]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 71113166Methyl 1-(4-((3-(hydroxy(phenyl)methyl)phenoxy)-methyl)phenyl)cyclopropanecarboxylate

Product 1

HCID 71093144Methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylateYield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 1-(4-((3-(hydroxy(phenyl)methyl)phenoxy)-methyl)phenyl)cyclopropanecarboxylate (1.824 g, 4.695 mmol) in toluene (21.8 mL) under an atmosphere of nitrogen, was added diphenylphosphoryl azide (1.21 mL, 5.635 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.84 mL, 5.635 mmol). The reaction mixture was stirred at 100° C. for 3 hours and then allowed to cool to room temperature. The reaction was quenched by addition of saturated aqueous ammonium chloride solution and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine and dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford a brown oil. The crude material was purified by silica gel chromatography eluting with 0-14% ethyl acetate in iso-hexane to afford the title compound as a colourless oil (1.214 g, 62%).

Workup

  1. temperatureto cool to room temperature
  2. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford a brown oil
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with 0-14% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-cfa63eb41a72444bbb11ca6bf94abd95
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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