Water → 2-Benzyl-5-methyloctahydropyrrolo[3,4-c]pyrrole

HRID 1174700Notes

Reaction equation

HRID 1174700 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=O)[N:14]([CH3:17])[C:15](=O)[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:11]([CH2:13][N:14]([CH3:17])[CH2:15]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 109337245-Benzyl-2-methyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 129585342-Benzyl-5-methyloctahydropyrrolo[3,4-c]pyrrole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-benzyl-2-methyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione (3.6 g) in THF (15 ml) was added dropwise to a suspension of lithium aluminum hydride (1.68 g) in THF (20 ml) while cooling in ice. The mixture was heated to reflux for 4 hours and then, at 0° C., water (1.8 ml), sodium hydroxide solution (10 M; 1.8 ml) and water (2.5 ml) were cautiously added. The precipitate was filtered off with suction and washed with ethyl acetate. The filtrate was concentrated. The product with the molecular weight of 216.33 (C14H2ON2); MS (ESI): 217 (M+H+) was obtained in this way.

Workup

  1. temperaturewhile cooling in ice
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 4 hours
  4. filtrationThe precipitate was filtered off with suction
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. customMS (ESI): 217 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-72adea9d59764201975874ad28057497
Source dataset
uspto-grants-2010_11
Patent number
US07838547B2

Reaction notes

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