Triethylamine → 2-Acetylhexahydrocyclopenta[c]pyrrol-5(1H)-one

Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (717 mg, 3 mmol) was dissolved in 20 mL of acetonitrile followed by addition of di-tert-butyl dicarbonate (0.42 mL, 4.5 mmol) and triethylamine (0.98 mL, 9 mmol) upon cooling by an ice-water bath. The reaction mixture was stirred overnight at the same temperature. The mixture was concentrated 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-acetyl-hexahydro-cyclopenta[c]pyrrol-5-one 5a (0.36 g, yield 72%) as a colorless oil

1. temperatureupon cooling by an ice-water bath
2. concentrationThe mixture was concentrated
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
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-b78de520f6154ac6834b0250ae7fb926

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415349B2