5-Benzyl-octahydropyrrolo(3,4-c)pyrrole-1,3-dione → 2-Benzyloctahydropyrrolo[3,4-c]pyrrole

HRID 712417

Reaction equation

HRID 712417 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=O)[NH:14][C:15](=O)[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:11]([CH2:13][NH:14][CH2:15]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 45649025-Benzyl-octahydropyrrolo(3,4-c)pyrrole-1,3-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 44543872-Benzyloctahydropyrrolo[3,4-c]pyrroleYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (3.88 g) in THF (80 mL) at −5° C. was added LiAlH4 (1.92 g) slowly. The reaction mixture was heated to reflux for 4 h, and then quenched with water, the mixture was extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 200:30:1 (v/v) DCM/MeOH/NH3H2O) to give the title compound as oil (2.07 g, 61.00%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. customquenched with water
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4 for 1 h
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was chromatographed with a silica gel column (eluting agent: 200:30:1 (v/v) DCM/MeOH/NH3H2O)

Sources & evidence

ORD record
ord-8a6356a0510f459d86a9cf54cc9f2527
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Linked notes

Loading…