3-Hydroxypicolinic Acid → (2R,3S)-3-hydroxypiperidine-2-carboxylic acid

HRID 1612075Notes

Reaction equation

HRID 1612075 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH4+].[OH-]>[Rh].O>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 134013-Hydroxypicolinic AcidHCID 14923Ammonium Hydroxide

Product 1

HCID 11094754(2R,3S)-3-hydroxypiperidine-2-carboxylic acidYield 11.3%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 3-hydroxypicolinic acid (1 g, 7.19 mmol) and 5 wt. % rhodium on carbon (200 mg) in a mixed solvents of conc. NH4OH (35 mL) and water (5 mL) in a pressure bottle was stirred under hydrogen at 80 psi overnight. The reaction mixture was filtered and the filtrate concentrated in vacuo to dryness to give 118 mg of the title compound (racemate). MS (ES): m/z 146 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-9b4ab97ce15348dba274f9394efde37d
Source dataset
uspto-grants-2006_01
Patent number
US06992102B2

Reaction notes

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