Ethanol → 1-Azabicyclo[3.2.2]nonan-3-one

To a 250 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 1.55 g (39.69 g-atm.) potassium and 80 mL toluene. The mixture was heated to reflux and treated with 1.83 mL (39.69 mmol) ethanol. Refluxing continued until the potassium disappeared. Then 4.08 g (15.87 mmol) ethyl-N-ethoxycarbonylmethyl-perhydroazepine-4-carboxylate was added and refluxing was continued for 14 hours. The reaction was evaporated and the residue taken up in 100 mL 1N hydrochloric acid. This solution was refluxed for 22 hours, cooled, washed with methylene chloride, and adjusted to pH 12 with 6N sodium hydroxide. The aqueous layer was extracted with methylene chloride, which was dried over sodium sulfate and evaporated. The resulting foam, 700 mg (32%), was used directly below.

1. customTo a 250 mL round-bottomed flask equipped with condenser and nitrogen inlet
2. temperatureThe mixture was heated
3. temperatureto reflux
4. temperatureRefluxing
5. temperaturerefluxing
6. customThe reaction was evaporated
7. temperatureThis solution was refluxed for 22 hours
8. temperaturecooled
9. washwashed with methylene chloride
10. extractionThe aqueous layer was extracted with methylene chloride, which
11. dry with materialwas dried over sodium sulfate
12. customevaporated

ORD record

ord-79a43229080347df830929827b8dc9aa

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05373003