5-Hydroxyindole → 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-hydroxy-1H-indole

HRID 1458964Notes

Reaction equation

HRID 1458964 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=O)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CO>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH:21]=[C:22]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=3)[NH:8][CH:7]=2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 160545-HydroxyindoleHCID 5360545SodiumHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 158394613-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-hydroxy-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium (4.8 g; 210 mmol) in dry methanol (130 ml), there are added, at room temperature, 5-hydroxyindole (4 g; 30.04 mmol) and N-(tert-butoxycarbonyl)piperidone (8.9 g; 45.1 mmol).

Sources & evidence

ORD record
ord-d47bc106135b4d199a1346fcd12d3df1
Source dataset
uspto-grants-1998_12
Patent number
US05852049

Reaction notes

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