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

0.1 ml of triethylsilane (0.63 mmol) 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 mmol) 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 (2f) (yield: 47%).

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

ORD record

ord-68204882faf549c18dd1a25382d9ac85

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846963B2