Hydrochloric Acid → Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (137 mg, 0.187 mmol) was added to a solution of benzyl 4-[3-bromo-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate (795 mg, 1.87 mmol) in ether (6 mL). The reaction mixture was cooled to 0° C. and cyclopropylmagnesium bromide (0.544 g, 3.75 mmol) was added. After 1 h, the mixture was warmed to ambient temperature. After 1 h, the mixture was cooled back to 0° C. and two additional portions of dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (137 mg, 0.187 mmol) and cyclopropylmagnesium bromide (544 mg, 3.75 mmol) were added. The mixture was warmed to ambient temperature. After 18 h, hydrochloric acid (10% in water) was added and the mixture was extracted with ether (2×). The combined organic extracts were washed with saturated aqueous sodium bicarbonate, water, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (173 mg). MS 386.2 (M+1).

Provenance & Evidence