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

Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (574 mg, 2.4 mmol) was dissolved in 20 mL of acetonitrile with stirring followed by addition of potassium carbonate (0.397 g, 2.88 mmol), and morpholine-4-carbonyl chloride (0.323 mL, 2.64 mmol) upon cooling by an ice-water bath. The reaction mixture was reacted overnight at the same temperature. 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, 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 2-(morpholine-4-carbonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 7a (0.572 g, yield 77.3%) as a colorless oil.

1. temperatureupon cooling by an ice-water bath
2. customThe reaction mixture was reacted overnight at the same temperature
3. concentrationThe mixture was concentrated under reduced pressure
4. additiondiluted with 50 mL of water
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 resulting residue was purified by silica gel column chromatography

ORD record

ord-7b22c4eef00c4c7085b6a84c04ccca94

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415349B2