1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 15754292, compound

HRID 1461667Notes

Reaction equation

HRID 1461667 reaction equation
C(O[CH:5]1[CH2:9][N:8]([C:10]([CH3:18])([CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:19])[CH:6]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH3:18][C:10]([N:8]1[CH2:9][CH:5]=[C:6]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:7]1=[O:19])([CH3:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19978936HCID 19978936, compound

Product 1

HCID 15754292HCID 15754292, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.7 g (2 mmol) of 4-acetoxy-1-(α,α-dimethylbenzyl)-3-phenyl-2-pyrrolidinone prepared by the method of Reference Example 15, was dissolved in 30 ml of toluene, and 0.36 g (2.4 mmol) of DBU was added thereto. The mixture was refluxed under heating for five minutes. The reaction solution was cooled, and toluene was added. The toluene solution was thoroughly washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The crude product thereby obtained was purified by silica gel column chromatography to obtain 0.4 g (yield: 73%) of the desired compound.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for five minutes
  3. temperatureThe reaction solution was cooled
  4. washThe toluene solution was thoroughly washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe crude product thereby obtained
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-976b1343886145febd4c9acae2fb76cb
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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