Ammonia → 6-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridine

HRID 2256081Notes

Reaction equation

HRID 2256081 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:22](=O)[CH:21]2[CH:16]([NH:17][CH2:18][CH2:19][CH2:20]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.N>C1COCC1>[CH2:7]([N:14]1[CH2:22][CH:21]2[CH:16]([NH:17][CH2:18][CH2:19][CH2:20]2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962Water2×HCID 9899604Tetrahydro-6-(phenylmethyl)-1H-pyrrolo(3,4-b)pyridine-5,7(2H,6H)-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 113563766-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridineYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of anhydrous THF was suspended 4.9 g of lithium aluminum hydride, and a solution of 3 g of 6-benzyl -5,7-dioxo-octahydropyrrolo[3.4-b]pyridine in 50 ml of anhydrous THF was added thereto dropwise with stirring while cooling with ice. After the addition, the reaction mixture was heated under reflux for 6 hours. After completion of the reaction, 4.9 ml of water, 4.9 ml of aqueous ammonia, and 15 ml of water were added to the reaction mixture in this order while cooling with ice, followed by stirring for 30 minutes. The reaction mixture was filtered through Celite®, and the filter cake was washed with THF (100 ml×4). The combined filtrate and washings were dried over anhydrous sodium sulfate and concentrated to yield 2.49 g of the titled compound as an oily substance.

Workup

  1. temperaturewhile cooling with ice
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 6 hours
  5. additionwere added to the reaction mixture in this order
  6. temperaturewhile cooling with ice
  7. stirringby stirring for 30 minutes
  8. filtrationThe reaction mixture was filtered through Celite®
  9. washthe filter cake was washed with THF (100 ml×4)
  10. dry with materialThe combined filtrate and washings were dried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3cc9081aeb8d4e488b3ced1323914a2a
Source dataset
uspto-grants-1997_08
Patent number
US05654318

Reaction notes

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