Ethyl Acetate → HCID 66755141, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromopyridine (22.47 mmol, 2 eq) was dissolved in diethyl ether (10 ml) and the solution was added dropwise to a solution of n-BuLi (24.7 mmol, 2.2 eq) in diethyl ether (70 ml) at −78° C. The resulting mixture was stirred for 30 min. tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (for the synthesis see above) (11.23 mmol, 1 eq.) was dissolved in diethyl ether (10 ml), the solution was slowly added, and the reaction mixture was then stirred at −78° C. for 1 h. The reaction mixture was warmed to room temperature, ethyl acetate (150 ml) and water (80 ml) were added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×70 ml) and the combined organic phases were dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (2% methanol in methylene chloride). Yield: 19%

Provenance & Evidence