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

HRID 751158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751158
[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]

Komponenten

6

Edukt 1

HCID 134013-Hydroxypicolinic Acid

Produkt 1

HCID 11094754(2R,3S)-3-hydroxypiperidine-2-carboxylic acidAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 88993Rhodium hydroxide (Rh(OH)3)KatalysatorHCID 9942167Palladium hydroxideKatalysatorHCID 962WaterLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

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]+

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4fc936a29cc54a14a0d4bbf0bedc3dd9
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

Notizen zur Reaktion

Wird geladen…