Triethylsilane → Methyl 3-(2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoate

HRID 2240590Notes

Reaction equation

HRID 2240590 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10](=[O:30])[CH2:11][CH2:12][C:13]1[C:14](=[O:29])[N:15](CC2C=CC(OC)=CC=2OC)[CH2:16][CH:17]=1>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10](=[O:30])[CH2:11][CH2:12][C:13]1[C:14](=[O:29])[NH:15][CH2:16][CH:17]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 57443412HCID 57443412, compound

Product 1

HCID 57443424Methyl 3-(2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoateYield 47.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.1 ml of triethylsilane (0.63 mM) was added to the reaction solution containing 200 mg of 3-[1-(2,4-dimethoxybenzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid methyl ester (0.63 mM) dissolved in 0.7 ml of trifluoroacetic acid solution at 0° C. After the reaction mixture was heated for 1 hr, the mixture was filtered and concentrated in vacuo to remove solvent. Then the resulting mixture was dissolved in 20 ml of chloroform solution to separate into an organic layer and water layer. The organic layer was washed with 5 ml of saturated NaHCO3 solution and 5 ml of saturated NaCl solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with EtOAc and hexanes (19:1) as an eluant to give 50 mg of 3-(2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-propionic acid methyl ester (20 (yield: 47%).

Workup

  1. temperatureAfter the reaction mixture was heated for 1 hr
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto remove solvent
  5. dissolutionThen the resulting mixture was dissolved in 20 ml of chloroform solution
  6. customto separate into an organic layer and water layer
  7. washThe organic layer was washed with 5 ml of saturated NaHCO3 solution and 5 ml of saturated NaCl solution
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
  12. additionmixed with EtOAc and hexanes (19:1) as an eluant

Sources & evidence

ORD record
ord-0dc1d4572f0d49fea1ac079611206041
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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