Acetonitrile → Methyl 5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxamide

Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (0.559 g, 2.34 mmol) was dissolved in 20 mL of acetonitrile. Upon cooling by an ice-water bath, potassium carbonate (0.646 g, 4.68 mmol) and methyl 2-chloroacetate (0.22 mL, 2.8 mmol) added successively. The reaction mixture was warmed up to room temperature and stirred overnight. The mixture was concentrated under reduced pressure and diluted with 50 mL of water. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic extracts were washed with 50 mL of saturated brine and 50 mL of water successively, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxamide 2a (0.25 g, yield 58.4%) as a colorless oil.

1. temperatureUpon cooling by an ice-water bath
2. concentrationThe mixture was concentrated under reduced pressure
3. additiondiluted with 50 mL of water
4. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
5. washThe combined organic extracts were washed with 50 mL of saturated brine and 50 mL of water successively
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-1ae4e67c12ab4e6b9f4f4d68257e94b5

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415349B2