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

HRID 872409

Reaktionsgleichung

Reaktionsgleichung von HRID 872409
[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-b0ee208866054cd0bebe63a8c6e36b21
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975285B2

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