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

HRID 872409

Reaction equation

HRID 872409 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 179991481-(2-Aminopyridin-4-yl)ethanolYield 45.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-b0ee208866054cd0bebe63a8c6e36b21
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Linked notes

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