Water → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

25 g of tropinone was dissolved in 100 mL of chloroform, and 50 mL of chloroethyl chloroformate was added thereto and stirred at room temperature for 6 hours. The reaction liquid was concentrated, 100 mL of methanol was added thereto, and heated overnight under reflux. The reaction liquid was cooled to room temperature and concentrated, and the resulting crude product was dissolved in 80 mL of N-methylpyrrolidone. 43 mL of benzyl bromide and 99 g of potassium carbonate were added thereto and stirred overnight at room temperature. The reaction liquid was poured into water, and extracted three times with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure to obtain 29.5 g of the entitled compound as a pale yellow liquid.

1. customThe reaction liquid
2. concentrationwas concentrated
3. addition100 mL of methanol was added
4. temperatureheated overnight
5. temperatureunder reflux
6. customThe reaction liquid
7. temperaturewas cooled to room temperature
8. concentrationconcentrated
9. dissolutionthe resulting crude product was dissolved in 80 mL of N-methylpyrrolidone
10. addition43 mL of benzyl bromide and 99 g of potassium carbonate were added
11. stirringstirred overnight at room temperature
12. customThe reaction liquid
13. extractionextracted three times with ethyl acetate
14. washThe organic layer was washed with water and saturated saline water
15. dry with materialdried with anhydrous magnesium sulfate
16. customthe solvent was evaporated off under reduced pressure

ORD record

ord-d12c9a93d1494df3a48197909c0cc616

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855294B2