Potassium Cyanide → HCID 67354921, compound

Participants

Reaction Steps

Azetidine (29.9 mmol, 10 eq) was added to a solution of tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (2.99 mmol, 1 eq) in methanol (15 ml) and acetic acid (1.5 ml) at 0° C. Then potassium cyanide (7.47 mmol, 2.5 eq) was added to the reaction mixture and it was stirred for another 16 h. The reaction mixture was slowly quenched with NH4OH solution (50 g ice+50 ml ammonia liquor) and stirred at 0° C. for another 30 min. The mixture was extracted with ethyl acetate. The organic layer was washed with water (15 ml), saturated ferrous sulfate solution (15 ml) and brine (20 ml) successively, dried over Na2SO4 and concentrated under reduced pressure to give the crude product. A solution of the crude product (1.1 g) in THF (30 ml) was added to an ice-cold solution of phenyl magnesium bromide (5 eq., 1 M solution in THF) and the resulting reaction mixture was stirred at 25° C. for 16 h under a nitrogen atmosphere. The reaction mixture was quenched with saturated ammonia solution under ice-cold conditions and extracted with ethyl acetate. The organic layer was washed with water (10 ml) and brine (10 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (25% EtOH in hexanes) to yield the desired product. Yield: 22%

Provenance & Evidence