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

HRID 501643Notes

Reaction equation

HRID 501643 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1>[OH-].[NH4+].O.[OH-].[Rh+3].[OH-].[OH-].[OH-].[OH-].[Pd+2]>[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

6

Reactant 1

HCID 134013-Hydroxypicolinic Acid

Product 1

HCID 11094754(2R,3S)-3-hydroxypiperidine-2-carboxylic acidYield 93.2%

Reagents, catalysts & solvents 4

HCID 88993Rhodium hydroxide (Rh(OH)3)CatalystHCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 3-hydroxy picolinic acid (20 g, 0.14 mol), 10% rhodium hydroxide on carbon (The catalyst was prepared according to the literature procedure: William M. Pealman, Tetrahedron Letters, 1967, 8, 1663-1664) (13.2 g), 20% palladium hydroxide on carbon (4.0 g) in 30% ammonium hydroxide solution (40 mL) and water (280 mL) were stirred under hydrogen at 75 psi for 6 days. The catalysts were removed by filtration and the filtrate was concentrated to yield the crude product 77A as a white foam (18.93 g): MS (ES): m/z 146 [M+1]+

Workup

  1. customwas prepared
  2. customThe catalysts were removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7d250a08beb44c5ab70bea48352b4133
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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