4-(1-Bromo-1-phenyl-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester → HCID 67046508, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-trimethylstannyl-5-carboxyethylpyridine (0.298 g, 0.949 mmol) and 4-(1-bromo-1-phenyl-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.334 mL, 0.949 mmol) in dry THF (5 mL) was degassed with a stream of Ar bubbles for 10 min. To this solution was added bis(triphenylphosphine)palladium dichloride (0.033 g, 0.047 mmol) and then the reaction vessel was sealed and the mixture was heated at 90° C. (oil bath temperature) for 16 h. The cooled mixture was then evaporated to dryness and the residue chromatographed (SiO2/hexane-EtOAc, 7:3) to give the title compound (0.294 g, 73%) as a clear yellow oil:

Provenance & Evidence