Tetrahydro-beta-carboline → Beta-Carboline

HRID 1423275Notes

Reaction equation

HRID 1423275 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1>C1(C)C(C)=CC=CC=1.[Pd]>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 1

HCID 107838Tetrahydro-beta-carboline

Product 1

HCID 64961Beta-Carboline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

To a solution of the crude tetrahydro β-carboline 3 in xylene (10 ml) was added 10% Pd/C (50-100 mg) and the mixture refluxed overnight. The reaction mixture was then cooled and filtered through celite and washed with MeOH (5-10 ml). Evaporation of the xylene/MeOH filtrate under reduced pressure yielded a crude β-carboline residue. The crude residue was subjected to flash chromatography (30% ethyl acetate in hexanes) to obtain pure β-carbolines 4 in 50-75% overall yield.

Workup

  1. temperaturethe mixture refluxed overnight
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered through celite
  4. washwashed with MeOH (5-10 ml)
  5. customEvaporation of the xylene/MeOH filtrate under reduced pressure

Sources & evidence

ORD record
ord-776bb236aee74a36aad73b03cf80ca68
Source dataset
uspto-grants-2015_01
Patent number
US08927570B2

Reaction notes

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