Triphenylphosphine → HCID 11404273, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl azodicarboxylate (18.2 ml, 115 mmol) in THF (100 ml) was added dropwise to a solution of Z-(2S,3R)-1-tert-butoxycarbonyl-3-(3-hydroxyprop-1-en-1-yl)-2-phenylpiperidin-3-ol (Description 20; 32 g, 96 mmol) and triphenylphosphine (30.2 g, 115 mmol) in THF (700 ml). The mixture was stirred at 0° C. for 30 minutes then at room temperature for 1.5 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with hexane/ethyl acetate (95:5 increasing to 80:20) to give the title compound as a colorless solid (23.4 g, 77%). MS (ES+) m/z 316 (M+ +1, 100%). 1H NMR (CDCl3) δ 7.45 (2H, d, J 7.4 Hz), 7.27 (2H, t, J 7.4 Hz), 7.20 (1H, t, J 7.4 Hz), 6.03 (1H, dt, J 6.1, 2.0 Hz), 5.68 (1H, dt, J 6.1, 2.0 Hz), 5.06 (1H, s), 4.61 (1H, dt, J 13.1, 2.0 Hz), 4.32 (1H, dt, J 13.1, 2.0 Hz), 4.08 (1H, m), 3.05 (1H, m), 2.05 (1H, m), 1.75 (3H, m), and 1.37 (9H, s).

Provenance & Evidence