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

HRID 2043085Notes

Reaction equation

HRID 2043085 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 (C14H20N2); 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-9a64b925a2394f6aaa1e5ac213d144ae
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

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