Ethyl benzoylacetate → HCID 10923588, compound

HRID 724828Notes

Reaction equation

HRID 724828 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH3-]C#N.[Na+]>CO>[C:10]1([CH:9]([NH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 8870Benzenamine hydrochloride (1:1)HCID 5003444Sodium cyanoborohydride

Product 1

HCID 10923588HCID 10923588, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of aniline hydrochloride (3.37 g, 26 mmol) and ethyl benzoylacetate (5 mL, 26 mmol) in MeOH (70 mL) was added NaBH3CN (1.75 g) and the mixture was stirred at room temperature for 18 h. The solvent was removed and the residue partitioned between 0.5N HCl and Et20. The aqueous phase was made basic with 1N NaOH and extracted with CHCl3. The organic phase was dried and concentrated to a residue. Purification by chromatography on silica gel (hexane: EtOAc, 5%) afforded ethyl 3-phenyl-3-(phenylamino)propionate (4.3 g, 62%). This compound was then hydrolized under basic conditions to give the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between 0.5N HCl and Et20
  3. extractionextracted with CHCl3
  4. customThe organic phase was dried
  5. concentrationconcentrated to a residue
  6. customPurification by chromatography on silica gel (hexane: EtOAc, 5%)

Sources & evidence

ORD record
ord-9ec9191673d841cb80b2ff1164cfb320
Source dataset
uspto-grants-1998_01
Patent number
US05705504

Reaction notes

Loading…