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

HRID 434080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 434080
[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]

Komponenten

5

Edukt 2

HCID 134013-Hydroxypicolinic AcidHCID 14923Ammonium Hydroxide

Produkt 1

HCID 11094754(2R,3S)-3-hydroxypiperidine-2-carboxylic acidAusbeute 11,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d0c3783aae3a487cb55cea6836ef6117
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670386B2

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