Tributylstannane → HCID 70228035, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2S,3R)-ethyl 3-(1-tert-butoxycarbonyl-3-hydroxy-2-phenylpiperidin-3-yl)propynoate (Description 9, 524 mg, 1.4 mmol) and tetrakis(triphenylphosphine)palladium (0) (50 mg) in toluene (10 ml) was degassed with nitrogen for 30 min. Tributyl tin hydride (0.405 mM, 1.5 mmol) was added dropwise and the resulting mixture was stirred at 23° C. for 2 h. The solvent was evaporated under reduced pressure and the residue was taken up in ethyl acetate (50 ml). The mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the title compound as a gum (538 mg, 0.87 mmol, 62%). 1H NMR (250 MHz, CDCl3) δ7.63 (1H, s), 7.30 (5H, m), 5.11 (1H, m, 310 (1H, m) 2.19 (1H, m), 1.80 (3H, m), 1.30-150 (12H, m), 1.40 (9H), s), 1.02 (6H), m), and 0.88 (9H), t, J 7.22 Hz), m/z (ES+) 619 (M+1)

Provenance & Evidence