1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22114259, compound

HRID 565102Notes

Reaction equation

HRID 565102 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][CH2:14][C:13](=[O:16])[C:12]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)(=O)=O.C1CCN2C(=NCCC2)CC1>CO>[CH3:1][S:2][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH2:15][CH2:14][C:13](=[O:16])[C:12]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10758665HCID 10758665, compound

Product 1

HCID 22114259HCID 22114259, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To the diketone of Step 1 (120 mg) in methanol (80 mL) was added DBU (0.1 mL). The resulting mixture was heated at 60° C. for 18 h. The methanol was then evaporated and to the crude mixture was added saturated aqueous ammonium chloride, the mixture was then extracted with EtOAc, the organic layer was dried over MgSO4, filtered, and the solvent evaporated under vacuum. The residue was purified by silica gel chromatography (20% EtOAc/hexane) to afford the title compound.

Workup

  1. customThe methanol was then evaporated and to the crude mixture
  2. additionwas added saturated aqueous ammonium chloride
  3. extractionthe mixture was then extracted with EtOAc
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum
  7. customThe residue was purified by silica gel chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-f503a3f5e0074767971f427459568a04
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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