Sodium borohydride → 1-(2-Aminopyridin-4-yl)ethanol

HRID 1916808

Reaktionsgleichung

Reaktionsgleichung von HRID 1916808
[NH2:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 131452581-(2-Aminopyridin-4-yl)ethan-1-one

Produkt 1

HCID 179991481-(2-Aminopyridin-4-yl)ethanolAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of 1-(2-aminopyridin-4-yl)ethanone (21) (168 mg, 1.234 mmol) in MeOH (10 mL), under nitrogen at 0° C., was added sodium borohydride (46.7 mg, 1.234 mmol). The resulting reaction mixture was stirred at RT for 2 hr, and then the solvents were removed under reduced pressure. The residue was taken up into EtOAc (25 mL), and extracted with saturated aq NaHCO3 solution (30 mL) and the layers separated. The aqueous layer was extracted with EtOAc (20 mL×2), and the combined organic extracts were washed with brine (30 mL), dried and the solvents removed under reduced pressure, to give 1-(2-aminopyridin-4-yl)ethanol (22) (77 mg, 45%) as a yellow oil: m/z 139 (M+H)+ (ES+).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customthe solvents were removed under reduced pressure
  3. extractionextracted with saturated aq NaHCO3 solution (30 mL)
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with EtOAc (20 mL×2)
  6. washthe combined organic extracts were washed with brine (30 mL)
  7. customdried
  8. customthe solvents removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b8d9497fde23420f91443ef216f526a3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618140B2

Verknüpfte Notizen

Wird geladen…