Tetrahydrofuran → HCID 22263187, compound

Participants

Reaction Steps

To a solution of (3R)-1′-(anthracene-9-carbonyl)-[1,4′]bipiperidinyl-3-carboxylic acid diethylamide (Intermediate 22, 22.2 mg, 47 μmol) in anhydrous tetrahydrofuran (0.5 mL) under nitrogen at −25° C. was added a solution of ethylmagnesium bromide (1M in tetrahydrofuran, 2.1 eq., 0.1 mL). The solution was allowed to warm to ambient temperature and after 30 min a further addition of ethylmagnesium bromide (1M in tetrahydrofuran, 4.2 eq., 0.2 mL) was made. The mixture was stirred for 16 hr at ambient temperature before quenching with methanol. The mixture was diluted with dichloromethane, washed with a mixture of sodium hydroxide and sodium hydrogen carbonate solutions, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under vacuum. The crude product was purified by chromatography on silica gel eluting with a 1%-10% methanol-dichloromethane gradient to give the title compound (3.2 mg, 15%).

Provenance & Evidence