Water → HCID 12149155, compound

HRID 1267948Notes

Reaction equation

HRID 1267948 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH2:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][N:16]=[CH:15][C:14]=1[O:21][CH3:22])C.O>C1COCC1>[CH3:20][O:19][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([O:21][CH3:22])[C:13]=1[CH2:12][CH2:11][CH2:10][OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 696798553-(3,5-Dimethoxypyridin-4-yl)propionic acid ethyl ester

Product 1

HCID 12149155HCID 12149155, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.1 g, 30 mmol) is suspended in THF (50 ml), and thereto is added with stirring 3-(3,5-dimethoxypyridin-4-yl)propionic acid ethyl ester (3.5 g, 15 mmol) obtained in Reference Example 22 at 50° C. over a period of time for 40 minutes. The mixture is further heated under reflux for 30 minutes, and thereto are added successively water (1.1 ml), a 15% aqueous sodium hydroxide solution (1.1 ml) and water (3.3 ml) in order to quench the reaction. The reaction solution is filtered, and the insoluble materials are removed, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol), and further recrystallized from isopropyl ether/hexane to give the title compound (2.9 g) as colorless crystals, m.p. 88-89° C.

Workup

  1. customobtained in Reference Example 22 at 50° C. over a period of time for 40 minutes
  2. temperatureThe mixture is further heated
  3. temperatureunder reflux for 30 minutes
  4. customa 15% aqueous sodium hydroxide solution (1.1 ml) and water (3.3 ml) in order to quench
  5. customthe reaction
  6. filtrationThe reaction solution is filtered
  7. customthe insoluble materials are removed
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)
  10. customfurther recrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-c4a9f0dfe1d748e88010d0ce3c53234b
Source dataset
uspto-grants-2003_04
Patent number
US06555557B1

Reaction notes

Loading…