Sodium Bicarbonate → (5-Fluoro-6-(pyrrolidin-1-yl)pyridin-3-yl)methanol

HRID 385592Notes

Reaction equation

HRID 385592 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:9]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:10][CH:11]=[C:12]([CH:17]=1)[C:13](OC)=[O:14].C(=O)([O-])O.[Na+]>C1COCC1>[F:7][C:8]1[CH:17]=[C:12]([CH2:13][OH:14])[CH:11]=[N:10][C:9]=1[N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 57815379Methyl 5-fluoro-6-(pyrrolidin-1-yl)nicotinate

Product 1

HCID 57815436(5-Fluoro-6-(pyrrolidin-1-yl)pyridin-3-yl)methanolYield 111%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.24 g of lithium aluminum hydride in 5 mL of THF, a solution of 0.70 g of methyl 5-fluoro-6-(pyrrolidin-1-yl)nicotinate in 5 mL of tetrahydrofuran was dropped under cooling with ice. After warming to room temperature, the mixture was stirred for 45 minutes, thereto was dropped a saturated aqueous sodium hydrogen carbonate solution under cooling with ice, and the mixture was stirred for 10 minutes. The reaction mixture was filtered, and the filtration residue was washed with ethyl acetate and water. The organic layer of the filtrate was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.68 g of (5-fluoro-6-(pyrrolidin-1-yl)pyridin-3-yl)methanol as a brown oily substance.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 10 minutes
  4. filtrationThe reaction mixture was filtered
  5. washthe filtration residue was washed with ethyl acetate and water
  6. customThe organic layer of the filtrate was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washthe resultant solution was washed with water
  9. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5163a8b65e4a4943b6d2e5e45336103a
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

Loading…