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

Hexahydro-cyclopenta[c]pyrrol-5-one triflutate 1f (717 mg, 3 mmol) was dissolved in 20 mL of dichloromethane, and 2-isocyanatopropane (9 mL, 9 mmol) and triethylamine(1.7 mL, 12 mmol) were then added to the solution in an ice-water bath. Upon completion of the addition, the reaction mixture was stirred overnight at room temperature, water (50 mL) was then added to the mixture. 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 residue was purified by silica gel column chromatography to obtain the title compound 5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid isopropylamide 6a (0.3 g, yield 47.6%) as a colorless oil.

1. additionUpon completion of the addition
2. extractionThe mixture was extracted with dichloromethane (50 mL×3)
3. washThe combined organic extracts were washed with 10% citric acid solution (50 mL) and 50 mL of saturated brine successively
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-fc571d4068e64d9380f7e275e3eca8b9

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178575B2