Sodium Sulfite → 3,8-Difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15137

Reaktionsgleichung

Reaktionsgleichung von HRID 15137
[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[C:7]([F:16])[C:8](=[O:15])[N:9]3CC(=C)C=1[C:10]=23.S([O-])([O-])=O.[Na+].[Na+].[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24].[OH2:28]>>[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[C:7]([F:16])[C:8](=[O:15])[N:9]3[CH2:25][C:23]([OH:27])([CH2:26][OH:28])[C:24]=1[C:10]=23

Komponenten

4

Edukt 3

HCID 24437Sodium SulfiteHCID 675274023,8-Difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneHCID 714019492-Methylpropan-2-ol--water (1/1)

Produkt 1

HCID 236342743,8-Difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneAusbeute 97 %

Versuchsvorschrift

A solution of 3,8-difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (631 mg, 2.9 mmol) in tert-butanol/water (30 ml/30 ml) was treated with AD mix alpha (4.3 g) under argon. After 18 hours stirring the reaction mixture was treated with saturated sodium sulphite solution (30 ml). After 10 minutes stirring the mixture was extracted with 20% methanol in dichloromethane (3×300 ml). The organic extracts were dried over magnesium sulphate and evaporated affording a white solid (710 mg, 97%).

Aufarbeitung

  1. additionmix alpha (4.3 g) under argon
  2. stirringAfter 10 minutes stirring the mixture
  3. extractionwas extracted with 20% methanol in dichloromethane (3×300 ml)
  4. dry with materialThe organic extracts were dried over magnesium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c9aded2d0f824bf9b94d7c7d4dcc8f67
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732460B2

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