Aluminium lithium hydride → 2-n-Butyl-1,2,3,4-tetrahydropyrrolo[3,4-b]indole

HRID 262159Notes

Reaction equation

HRID 262159 reaction equation
[CH2:1]([N:5]1[CH2:16][C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[C:6]1=O)[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([N:5]1[CH2:16][C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 213202522-butyl-1,4-dihydropyrrolo[3,4-b]indol-3(2H)-one

Product 1

HCID 213202552-n-Butyl-1,2,3,4-tetrahydropyrrolo[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-n-Butyl-1,4-dihydropyrrolo[3,4-b]indol-3(2H)-one, 20 g., in dry tetrahydrofuran, 400 ml., is added slowly to a slurry of LiAlH4, 14 g., in tetrahydrofuran, 250 ml. After refluxing twenty hours, the reaction mixture is hydrolyzed with 30 ml. of water, and filtered. After the solvent is removed, one obtains 20.1 g. of a reddish-brown solid. Recrystallization from methanol, 200 ml., gives 11 g. of the title compound, m.p. 151°-2°.

Workup

  1. temperatureAfter refluxing twenty hours
  2. filtrationof water, and filtered
  3. customAfter the solvent is removed
  4. customone obtains 20.1 g
  5. customRecrystallization from methanol, 200 ml
  6. custom, gives 11 g

Sources & evidence

ORD record
ord-ce6cb22447a14935accd10dbacc4aefa
Source dataset
uspto-grants-1979_05
Patent number
US04153711

Reaction notes

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