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

HRID 609698Notes

Reaction equation

HRID 609698 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1>[Pd].O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

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

Product 1

HCID 122292494-(5-hydroxyindol-3-yl)piperidineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (96 ml) was added to an argon degassed flask containing 4-(5-hydroxyindol-3-yl)-1,2,3,6-tetrahydropyridine (2.67 g, 7.64 mmol), [prepared as described in Step 1, above] and 10% Palladium on carbon (2.67 g). The reaction mixture was hydrogenated for 15 h at 60 psi on a parr apparatus. The reaction mixture was degassed, filtered through Celite and concentrated in vacuo to give 4-(5-hydroxyindol-3-yl)piperidine as a white solid (95%). This material was converted to 1-[4-(5-hydroxyindol-3-yl)piperidine-1-sulfonyl]piperidine-2-(RS)-carboxylic acid (99%) by proceeding as described in Example 16, Step 2 above, by substituting 4-(5-fluoroindol-3-yl)piperidine and 2-(R)-methoxycarbonylpiperidine-1-sulfamoyl chloride with 4-(5-hydroxyindol-3-yl)piperidine and 2-(RS)-methoxycarbonylpiperidine-1-sulfamoyl chloride respectively.

Workup

  1. additioncontaining
  2. customThe reaction mixture was degassed
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6078be03178f4c6395c4ddd52abf785a
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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