Water → 5-Benzyl-1-methyl-octahydropyrrolo[3,4-b]pyrrole

HRID 981087Notes

Reaction equation

HRID 981087 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:21](=O)[CH:20]2[CH:16]([N:17]([CH3:23])[CH2:18][CH2:19]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[K+]>O1CCCC1>[CH2:7]([N:14]1[CH2:21][CH:20]2[CH:16]([N:17]([CH3:23])[CH2:18][CH2:19]2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 15069999HCID 15069999, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 150700005-Benzyl-1-methyl-octahydropyrrolo[3,4-b]pyrrole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.52 g (40 mmol) of lithium aluminum hydride are initially introduced into 30 ml of anhydrous tetrahydrofuran, and 4.9 g (20 mmol) of 5-benzyl-4,6-dioxo-1-methyl-octahydropyrrolo[3,4-b]pyrrole are added dropwise as a solution in 15 ml of anhydrous tetrahydrofuran. The mixture is then subsequently stirred at the boiling point for 3 hours. 1.5 ml of water, 1.5 ml of 15% strength potassium hydroxide solution and 4.5 ml of water are added dropwise in succession to the batch and the precipitate is then filtered off with suction and washed with tetrahydrofuran. The filtrate is concentrated on a rotary evaporator and the residue is distilled. 3.1 g (72% of theory) of a colorless distillate of boiling point 80° C./0.07 mbar are obtained.

Workup

  1. filtrationthe precipitate is then filtered off with suction
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated on a rotary evaporator
  4. distillationthe residue is distilled
  5. custom3.1 g (72% of theory) of a colorless distillate of boiling point 80° C./0.07 mbar are obtained

Sources & evidence

ORD record
ord-37a06401e8e34245833bb1b13efc265a
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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