5-Hexyl-3-isopropyl-3(3-nitrophenyl)-3a,6a-dihydropyrrolo(3,4-c)pyrazole-4,6(3H,5H) dione → 3-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 428938Notes

Reaction equation

HRID 428938 reaction equation
[CH2:1]([N:7]1[C:14](=[O:15])[CH:13]2[CH:9](N=N[C:12]2([CH:25]([CH3:27])[CH3:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:8]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>O1CCOCC1>[CH2:1]([N:7]1[C:14](=[O:15])[CH:13]2[CH:9]([C:12]2([CH:25]([CH3:27])[CH3:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:8]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 221412935-Hexyl-3-isopropyl-3(3-nitrophenyl)-3a,6a-dihydropyrrolo(3,4-c)pyrazole-4,6(3H,5H) dione

Product 1

HCID 221412793-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 104.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Hexyl-3-isopropyl-3(3-nitrophenyl)-3a,6a-dihydropyrrolo(3,4-c)pyrazole-4,6(3H,5H) dione (Preparation 58, 0.65 g, 1.6 mmol) was dissolved in dioxan (25 ml) and heated under reflux for 3 h. The solvent was removed in vacuo and the oily residue dried in vacuum for 16 h at room temperature to give the crude product as a yellow solid. The crude product was purified by chromatography on a Biotage Flash 12M™ cartridge packed with silica gel (8 g), eluting with hexane:ethyl acetate (9:1) to give the title compound (0.60 g, 100%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. customthe oily residue dried in vacuum for 16 h at room temperature
  5. customto give the crude product as a yellow solid
  6. customThe crude product was purified by chromatography on a Biotage Flash 12M™ cartridge
  7. washeluting with hexane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-0690009612854ad597e61402dd319f8e
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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