Dichloromethane → HCID 19936399, compound

HRID 36870Notes

Reaction equation

HRID 36870 reaction equation
C(Cl)Cl.C[O:5][C:6]1[CH:21]=[CH:20][C:9]([CH2:10][N:11]2[NH:17][C:16](=[O:18])[CH:15]3[CH:13]([CH2:14]3)[C:12]2=[O:19])=[CH:8][CH:7]=1.B(Br)(Br)Br>O>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[NH:17][C:16](=[O:18])[CH:15]3[CH:13]([CH2:14]3)[C:12]2=[O:19])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 107768063-(4-Methoxy-benzyl)-3,4-diaza-bicyclo[4.1.0]heptan-2,5-dione

Product 1

HCID 19936399HCID 19936399, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 ml of methylene chloride was added 462 mg (1.87 mmol) of (±)-3-(4-methoxybenzyl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione obtained in Reference Example 19. The mixture was cooled on a dry ice/ethanol bath, and 0.1 ml (1.1 mmol) of boron tribromide was added thereto dropwise. The temperature was elevated to room temperature, and the mixture was stirred for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was recrystallized from ethanol/chloroform to obtain 120 mg (29.6%) of the titled compound.

Workup

  1. customobtained in Reference Example 19
  2. temperatureThe mixture was cooled on a dry ice/ethanol bath
  3. customwas elevated to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customthe residue was recrystallized from ethanol/chloroform

Sources & evidence

ORD record
ord-2154e15dceea4bc7b34faa003c458041
Source dataset
uspto-grants-1995_05
Patent number
US05418232

Reaction notes

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