Water → 3-[6-(2-Fluorophenyl)pyridin-3-yl]propan-1-ol

HRID 1896692Notes

Reaction equation

HRID 1896692 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[CH:11][CH:12]=1)C.[BH4-].[Li+].O>C1COCC1>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[N:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 68537058Ethyl 3-[6-(2-fluorophenyl)pyridin-3-yl]propanoate

Product 1

HCID 691058943-[6-(2-Fluorophenyl)pyridin-3-yl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 400 mg (1.46 mmol) of 3-(6-(2-fluorophenyl)pyridin-3-yl)propionic acid ethyl ester and 63.8 mg (2.93 mmol) of lithium borohydride were stirred in 20 ml of THF at 40° C. for 3 h. After cooling, the mixture was cautiously hydrolyzed with water, the precipitate was filtered off with suction, and water and methylene chloride were added to the filtrate. The organic phase was separated, washed with water and concentrated. Yield: 241 mg (71%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction, and water and methylene chloride
  3. additionwere added to the filtrate
  4. customThe organic phase was separated
  5. washwashed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-46c3041dae0141aaa168b5230838e062
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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