Sodium borohydride → HCID 66718147, compound

HRID 1514672Notes

Reaction equation

HRID 1514672 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:18])=[N:6][CH:5]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86646253HCID 86646253, compound

Product 1

HCID 66718147HCID 66718147, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-(5-formyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (0.25 g, 0.74 mmol) in methanol (10 mL) was treated at room temperature with sodium borohydride (0.03 g, 0.74 mmol) and stirred for 1 h. After quenching with aqueous citric acid (5 mL of a 10% solution) and extraction with ethyl acetate the organic phase was dried (Na2SO4) filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetete=90:10 to 40:60) afforded the title compound as a white solid (0.22 g, 89%). MS: m/e=341.1 [M+H]+.

Workup

  1. customAfter quenching with aqueous citric acid (5 mL of a 10% solution) and
  2. extractionextraction with ethyl acetate the organic phase
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica, heptane:ethyl acetete=90:10 to 40:60)

Sources & evidence

ORD record
ord-b521316f22974416a5f3885d5f17d784
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

Loading…