Boron tribromide → HCID 86679683, compound

HRID 577757Notes

Reaction equation

HRID 577757 reaction equation
[CH2:1]([N:8]1[CH2:12][C@:11]2([O:18]C)[C:13](=[O:17])[NH:14][C:15](=[O:16])[C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][C@:11]2([OH:18])[C:13](=[O:17])[NH:14][C:15](=[O:16])[C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86679679HCID 86679679, compound

Product 1

HCID 86679683HCID 86679683, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled −78° C. solution of (cis)-5-benzyl-3a-methoxytetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (403 mg, 1.55 mmol) in DCM (5.15 mL was added BBr3 (0.293 mL, 3.10 mmol). After 1 hr, the reaction mixture was warmed to 0° C. and stirred for an additional 1 hr and eventually warmed to rt and stirred for 24 hrs. The reaction mixture was cooled to 0° C., quenched with MeOH until the evolution of gas subsided. The mixture was concentrated and the residue was redissolved in MeOH (4 mL). Pd/C (40 mg) and was added and stirred under nitrogen to remove the borane (org letters, 2001, p 465-467) for 72 hrs. The mixture was filtered and concentrated to afford the crude title compound that was carried forward to the next step without further purification. m/z (APCI+) for C13H14N2O3 247.10 (M+H)+.

Workup

  1. temperatureeventually warmed to rt
  2. stirringstirred for 24 hrs
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched with MeOH until the evolution of gas
  5. concentrationThe mixture was concentrated
  6. dissolutionthe residue was redissolved in MeOH (4 mL)
  7. additionPd/C (40 mg) and was added
  8. stirringstirred under nitrogen
  9. customto remove the borane (org letters, 2001, p 465-467) for 72 hrs
  10. filtrationThe mixture was filtered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5408ff75d1b64e04a2a83d6da621d6f6
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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