Sodium Bicarbonate → 6-Oxopiperidine-3-carboxylic acid

HRID 741867Notes

Reaction equation

HRID 741867 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[H][H]>O.[Ru]>[C:6]([CH:5]1[CH2:4][NH:3][C:2](=[O:1])[CH2:10][CH2:9]1)([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, compoundHCID 178418479HCID 178418479, compound

Product 1

HCID 5600906-Oxopiperidine-3-carboxylic acidYield 72.9%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 962WaterSolvent

Procedure

To a suspension of 10.0 g of 6-hydroxynicotinic acid in 200 ml water were added 6.5 g of sodium bicarbonate. The resulting solution was subjected to 500 psig hydrogen at 100° C. for 12 hours in the presence of 2.5 g ruthenium on alumina. The catalyst was removed by filtration. The filtrate was acidified to. pH 4 with 6N HCl and evaporated to a colorless solid (~15 g ). The solid was treated with 40 ml methanol and filtered to remove most of the sodium chloride. The filtrate was evaporated to give 7.5 g of the title compound: MS m/z 143 (M+); 300-MHz 1H NMR (DMSO-d6) δ1.62-77 (m, 1H), 1.83-1.97 (m, 1H), 2.00-2.21 (m, 2H), 2.23-2.35 (m, 1H), 3.21 (d, J=8 Hz, 2H), 7, 28 (s, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. custompH 4 with 6N HCl and evaporated to a colorless solid (~15 g )
  3. additionThe solid was treated with 40 ml methanol
  4. filtrationfiltered
  5. customto remove most of the sodium chloride
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f1fdb8fdea9a411d9258d9411830911f
Source dataset
uspto-grants-1996_09
Patent number
US05552545

Reaction notes

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