Triethylamine → n-Isopropyl-5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxamide

Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (717 mg, 3 mmol) was dissolved in 20 mL of dichloromethane with stirring upon cooling by an ice-water bath, followed by addition of isocyanate (9 mL, 9 mmol) and triethylamine (1.7 mL, 12 mmol). The reaction mixture was reacted overnight at room temperature and diluted with 50 mL of water. The mixture was extracted with dichloromethane (50 mL×3). The combined organic extracts were washed with 10% citric acid solution (50 mL) and 50 mL of saturated brine successively, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain N-isopropyl-5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid isopropylamide 6a (0.3 g, yield 47.6%) as a colorless oil.

1. temperatureupon cooling by an ice-water bath
2. customThe reaction mixture was reacted overnight at room temperature
3. extractionThe mixture was extracted with dichloromethane (50 mL×3)
4. washThe combined organic extracts were washed with 10% citric acid solution (50 mL) and 50 mL of saturated brine successively
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-707e52611fe04a1c82561bf6b0237231

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415349B2