Sodium Sulfite → 1-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol

HRID 639022

Reaktionsgleichung

Reaktionsgleichung von HRID 639022
C(C1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)=C.S([O-])([O-])=O.[Na+].[Na+].[C:22]([OH:26])(C)([CH3:24])[CH3:23].[OH2:27]>>[F:15][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:23]=1[CH:22]([OH:26])[CH2:24][OH:27])=[N:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2

Komponenten

4

Edukt 3

HCID 24437Sodium SulfiteHCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineHCID 714019492-Methylpropan-2-ol--water (1/1)

Produkt 1

HCID 671345911-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediolAusbeute 96 %

Versuchsvorschrift

To a solution of AD-mixβ (50 g) in tert-butanol/water (200 mL/200 mL), cooled in an ice-bath for 30 minutes, 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (Preparation 6) (8 g, 39.2 mmol) was added and the reaction mixture was stirred at room temperature for 48 hours. Sodium sulfite (75 g) was added and the mixture was stirred for a further 30 minutes. It was extracted with diethyl ether then several times with 10% methanol in chloroform. The organic extract was evaporated under vacuum to afford the desired product as an oil (8.93 g, 96%). MS (+ve ion electrospray) m/z 239 (MH+); enantiomeric excess=44%, as determined by chiral analytical HPLC.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 30 minutes
  2. extractionIt was extracted with diethyl ether
  3. extractionThe organic extract
  4. customwas evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e503c4dd0dbb4ff59358036b82935dda
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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