Sodium borohydride → HCID 23506277, compound

HRID 1884587Notes

Reaction equation

HRID 1884587 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.[Cl-].[Na+].O>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23506261HCID 23506261, compound

Product 1

HCID 23506277HCID 23506277, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(3-Acetylphenoxy)-3-[3-(pyridin-4-yl)propoxy]pyridine (0.20 g, 0.3 mmol) obtained in Example 60 is dissolved in methanol (10 ml), and thereto is added sodium borohydride (0.50 g, 13 mmol), and the mixture is stirred at room temperature for 10 minutes. To the reaction solution is added a saturated brine (50 ml), and the mixture is extracted with ethyl acetate (100 ml). The organic layer is washed with a saturated brine (50 ml×2); dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol) to give 2-[3-(1-hydroxyethyl)phenoxy]-3-[3-(pyridin-4-yl)propoxy]pyridine, which is further treated with fumaric acid to give the title compound (0.06 g), m.p. 93-97° C. (recrystallized from ethanol/diethyl ether).

Workup

  1. extractionthe mixture is extracted with ethyl acetate (100 ml)
  2. washThe organic layer is washed with a saturated brine (50 ml×2)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-4021d149b4ae48cfab5f9691585cb940
Source dataset
uspto-grants-2004_07
Patent number
US06765095B2

Reaction notes

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