3-Butyn-2-ol → 4-(1-Phenyl-1-(3-hydroxy-1-butyn-1-yl)-methylene)-piperidine-1-carboxylic Acid Tert-Butyl Ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-(1-phenyl-1-iodomethylene)-piperidine-1-carboxylic acid tert-butyl ester (0.537 g, 1.60 mmol), PdCl2(PhCN)2 (0.032 g, 0.083 mmol), tri-2-furylphosphine (0.0806 g, 0.347 mmol), and CuI (0.034 g, 0.178 mmol) was added piperidine (10 mL), followed by 3-butyn-2-ol (0.25 mL, 3.19 mmol). The mixture was heated at 100° C. for 8 h and then the solvent was removed in vacuo. The residue was partitioned with EtOAc-H2O and the aqueous phase was separated and re-extracted with EtOAc (×2). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated, and the residue was purified by flash chromatography (SiO2/hexane:EtOAc, 3:2) to give the title compound (0.402 g, 73%) as a yellow orange oil which solidified on standing:

Provenance & Evidence