Glycolic Acid → 2-(2-Hydroxy-acetyl)-hexahydro-cyclopenta[c]pyrrol-5-one

Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f (764.8 mg, 3.2 mmol) and 2-hydroxyl ethanoic acid (267.5 mg, 3.52 mmol) were dissolved in 10 mL of acetonitrile. Upon cooling by an ice-water bath, hydroxyacetic acid (1.3 g, 9.6 mmol), 1-ethyl-3-dimethylaminopropyl-carbodiimide hydrochloride (1.23 g, 6.4 mmol) and triethylamine (1.3 mL, 9.6 mmol) were added. The ice-water bath was removed and the reaction mixture was reacted overnight at 25° C. The mixture was concentrated and diluted with 20 mL of ethyl acetate. The mixture was filtered under reduced pressure and the filtrate was washed with 20 mL of water. The organic phase was dried over anhydrous magnesium sulfate, filtered under reduced pressure and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 2-(2-hydroxy-acetyl)-hexahydro-cyclopenta[c]pyrrol-5-one 3a (0.375 g, yield 64%) as a colorless oil.

1. temperatureUpon cooling by an ice-water bath
2. customThe ice-water bath was removed
3. customthe reaction mixture was reacted overnight at 25° C
4. concentrationThe mixture was concentrated
5. additiondiluted with 20 mL of ethyl acetate
6. filtrationThe mixture was filtered under reduced pressure
7. washthe filtrate was washed with 20 mL of water
8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
9. filtrationfiltered under reduced pressure
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-e1e0c88314cc43fbb2edec8e1edfa0fd

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304411B2