Acetic Acid → tert-Butyl 4-(ethylamino)piperidine-1-carboxylate

To a stirred solution of 1-tert-butoxycarbonyl-4-piperidone (3.99 g, 20 mmol) in THF (40 mL) were added ethylamine (20 mL of a 2.0 M solution in THF, 40 mmol), acetic acid (1.15 mL, 20 mmol) and sodium triacetoxyborohydride (8.48 g, 40 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with 1 N aqueous sodium hydroxide (120 mL) at 0° C. and stirred at room temperature for 30 minutes. The organic solvent was evaporated under reduced pressure, and the remaining aqueous layer was extracted with ethyl acetate (40 mL, 2×20 mL). The combined organic layers were washed with brine (2×20 mL), dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to afford the title compound (4.54 g, 19.9 mmol, 99%) as a pale yellow oil.

1. customThe reaction mixture was quenched with 1 N aqueous sodium hydroxide (120 mL) at 0° C.
2. stirringstirred at room temperature for 30 minutes
3. customThe organic solvent was evaporated under reduced pressure
4. extractionthe remaining aqueous layer was extracted with ethyl acetate (40 mL, 2×20 mL)
5. washThe combined organic layers were washed with brine (2×20 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure

ORD record

ord-ad82ff0efc89415eb0d7427aa65fcf58

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562978B1