Water → 2-acetyl-2-azabicyclo[2.2.1]hept-5-en-3-one

100 g of (±)-2-azabicyclo[2.2.1 ]hept-5-en-3-one were dissolved in acetonitrile (800 ml) and pyridine (161.26 ml) under nitrogen. At 12° C., 104.5 g of acetyl chloride were added dropwise over the course of 2 hours. The mixture was then stirred at room temperature for 4.5 hours. 800 ml of water were added to the mixture, and the acetonitrile was evaporated off in vacuo. The aqueous phase was extracted 3 times with 400 ml of ethyl acetate. The combined org. phases were washed with 1N HCl (400 ml), water (400 ml), saturated NaCl (400 ml), dried with magnesium sulphate and completely evaporated. The residue was taken up in methylene chloride and filtered through silica gel. The filtrate was concentrated and the product was purified by distillation. 107.76 g of product were obtained as a clear liquid. The yield was 71%.

1. customthe acetonitrile was evaporated off in vacuo
2. extractionThe aqueous phase was extracted 3 times with 400 ml of ethyl acetate
3. washphases were washed with 1N HCl (400 ml), water (400 ml), saturated NaCl (400 ml)
4. dry with materialdried with magnesium sulphate
5. customcompletely evaporated
6. filtrationfiltered through silica gel
7. concentrationThe filtrate was concentrated
8. distillationthe product was purified by distillation

ORD record

ord-1f1b1ee50a1a4749b58a8f7aaa8c1997

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06368850B1