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

HRID 1602528Notes

Reaction equation

HRID 1602528 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-d068e6f3e84b44378e7128d4d044e37f
Source dataset
uspto-grants-1999_11
Patent number
US05981576

Reaction notes

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