5-Benzyl-4,6-dioxo-octahydropyrrolo[3,4-b]pyrrole → 5-Benzyl-octahydro-pyrrolo[3,4-b]pyrrole

HRID 974901Notes

Reaction equation

HRID 974901 reaction equation
[CH2:1]([N:8]1[C:15](=O)[CH:14]2[CH:10]([NH:11][CH2:12][CH2:13]2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([NH:11][CH2:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 150700035-Benzyl-4,6-dioxo-octahydropyrrolo[3,4-b]pyrroleHCID 21226445Aluminium lithium hydride

Product 1

HCID 150700045-Benzyl-octahydro-pyrrolo[3,4-b]pyrrole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

57.7 g (0.25 mol) of crude 5-benzyl-4,6-dioxo-octahydropyrrolo[3,4-b]pyrrole are reduced with 21.4 g (0.56 mol) of lithium aluminum hydride by boiling in 700 ml of absolute tetrahydrofuran for 10 hours in accordance with the working instructions of Example Ic. Working up by distillation gives 21.0 g (41.1% of theory) of an oil of boiling point 95° C./0.1 mbar.

Workup

  1. distillationWorking up by distillation
  2. customgives 21.0 g (41.1% of theory) of an oil of boiling point 95° C./0.1 mbar

Sources & evidence

ORD record
ord-66645e275728415b98435f766bb61bce
Source dataset
uspto-grants-1997_03
Patent number
US05607942

Reaction notes

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