5-Hydroxyindole → 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indol-5-ol

HRID 1856887Notes

Reaction equation

HRID 1856887 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.C(OC([N:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)=O)C1C=CC=CC=1>C(O)(C)(C)C.C(OCC)(=O)C>[OH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:30]1[CH2:31][CH2:32][NH:27][CH2:28][CH:29]=1

Participants

6

Reactant 3

HCID 160545-HydroxyindoleHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 156466783-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indol-5-olYield 92%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (2.81 g, 25.02 mmol) was added to a solution of 5-hydroxyindole (1.11 g, 8.34 mmol) in tert-butyl alcohol. 1-Benzyloxycarbonyl-4-piperidone (3.89 g, 16.67 mmol) was added to the purple reaction mixture at RT. After 16 h, the reaction mixture was diluted with ethyl acetate (100 ml) and washed with saturated sodium bicarbonate, brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed (SiO2, 25-45% ethyl acetate/hexanes) to give 4-(5-hydroxyindol-3-yl)-1,2,3,6-tetrahydropyridine as a white solid (92%).

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed (SiO2, 25-45% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-755429f28dfe4d1abbb9e556bb3e6063
Source dataset
uspto-grants-2000_11
Patent number
US06143744

Reaction notes

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