Potassium Carbonate → 2-(Morpholine-4-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one

Hexahydro-cyclopenta[c]pyrrol-5-one triflutate 1f (574 mg, 2.4 mmol) was dissolved in 20 mL of acetonitrile with stirring, and potassium carbonate (0.397 g, 2.88 mmol) was then added to the solution in an ice-water bath, followed by morpholine-4-carbonyl chloride (0.323 mL, 2.64 mmol). Upon completion of the addition, the reaction mixture was stirred overnight in an ice-water bath, then the solvent was evaporated, and water (50 mL) was added to the residue. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic extracts were washed with 50 mL of saturated brine, 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 2-(morpholine-4-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 7a (0.572 g, yield 77.3%) as a colorless oil.

1. additionUpon completion of the addition
2. stirringthe reaction mixture was stirred overnight in an ice-water bath
3. customthe solvent was evaporated
4. additionwater (50 mL) was added to the residue
5. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
6. washThe combined organic extracts were washed with 50 mL of saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-f5861fdefb8b4d89868acd3e1ae7b696

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178575B2