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

HRID 1916808

Reaction equation

HRID 1916808 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-b8d9497fde23420f91443ef216f526a3
Source dataset
uspto-grants-2013_12
Patent number
US08618140B2

Linked notes

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