Methyl chloroformate → 5-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid methyl ester

Hexahydro-cyclopenta[c]pyrrol-5-one triflutate 1f (0.559 g, 2.34 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (0.646 g, 4.68 mmol) and methyl chloroformate (0.22 mL, 2.8 mmol) were then added to the solution in an ice-water bath successively. Upon completion of the addition, the reaction mixture was allowed to increase to room temperature, and stilled overnight. The solvent was evaporated, and 50 mL of water was then 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 and 50 mL of water 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 methyl ester 2a (0.25 g, yield 58.4%) as a colorless oil.

1. additionUpon completion of the addition
2. customstilled overnight
3. customThe solvent was evaporated
4. addition50 mL of water was then 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 and 50 mL of water successively
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-16b9ebfe5e874ec4aa25347580305654

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178575B2