1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 131734197, compound

HRID 1497014Notes

Reaction equation

HRID 1497014 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[CH2:13]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([N:31]=[N+:32]=[N-:33])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:31]([CH2:13]/[CH:12]=[CH:11]/[CH:10]=[CH:9]/[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[N+:32]=[N-:33]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 88313714HCID 88313714, compound

Product 1

HCID 131734197HCID 131734197, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(2E,4E)-7-Phenylhepta-2,4-dien-1-ol (6.8 g) was dissolved in dry toluene (130 ml) and cooled in an ice-salt bath. Diphenyl phosphorazidate (7.83 ml) was added, followed by dropwise addition of DBU (6.53 ml) in dry toluene (15 ml). The mixture was stirred for 15 h while warming to room temperature. Solvents were evaporated and the residue was partitioned between diethyl ether and 1N NaOH. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography yielded a colorless liquid.

Workup

  1. temperaturecooled in an ice-salt bath
  2. customSolvents were evaporated
  3. customthe residue was partitioned between diethyl ether and 1N NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography
  9. customyielded a colorless liquid

Sources & evidence

ORD record
ord-71ca2fb6d91c400d9edaa1b38a2dd119
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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