Tributyltin hydride (7.8 ml, 29 mmol) was added dropwise to a degassed solution of 1-benzyl-3-(3-hydroxy-1-propyn-1-yl)piperidin-3-ol (Desc. 1; 5.91 g, 24.1 mmol) and tetrakis(trisphenylphosphine)palladium(0) (0.52 g, 0.45 mmol) in toluene (100 ml) at -5° C. The reaction mixture was stirred at -5° C. for 2 hours, allowed to warm up and concentrated in vacuo to afford an approximately 2.5:1 mixture of the title compound and isomeric 1-benzyl-3-(3-hydroxy-1-tributylstannyl-1-propen-1-yl)piperidin-3-ol. The mixture was purified by flash chromatography, eluting with ethyl acetate/hexane (1:2), to give the title compound (8.82 g, 68%; δH (250 MHz, CDCl3) 0.88 (15 H, m), 1.24-1.53 (14H, m), 1.78 (2H, m), 1.98 (1H, m), 2.11 (1H, d, J 11.1Hz), 2.69-2.80 (2H, m), 3.51 (1H, d, J. 13.2Hz, NCHACHBPh), 3.57 (1H, d, J 13.2Hz, NCHACHBPh), 4.44 (2H, br s, CH2OH), 5.38 (1H, br s, CH=C), 7.26-7.34 (5H, m ArH).
