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

HRID 843015Notes

Reaction equation

HRID 843015 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-3c8145339e8d457f89da06f3096a3958
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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