Tributylstannane → 1-methyl-4-((E)-2-tributylstannanyl-vinyl)-piperidin-4-ol

Participants

Reaction Steps

4-Ethynyl-1-methylpiperidin-4-ol (Exploratory Library; 3.34 g; 24 mmol) and PdCl2(PPh3)2 (337 mg; 0.48 mmol) were dissolved and stirred in THF (100 ml), cooled in a water bath to 180C, while Bu3SnH (7.6 ml; 28.8 mmol) was added dropwise within 3 minutes. The reaction mixture was stirred at room temperature for 4 hours, poured directly on a column of SiO2 and chromatographed (EtOAc/MeOH/NH3 95/5/0.5) to deliver the title compound as a greenish oil (3.45 g; 33%).

Provenance & Evidence