Triphenylphosphine → HCID 67239290, compound

Participants

Reaction Conditions

Reaction Steps

Diethylazodicarboxylate (40% solution in toluene, 3.4 mL, 7.4 mmol) was added to a mixture of 6-hydroxy-3,4-dihydro-2(1H)-quinolinone 2 (1.0 g, 6.1 mmol), triphenylphosphine (1.607 g, 6.1 mmol), and 1-boc-azetidine-3-yl-methanol 18 (1.148 g, 6.1 mmol) in anhydrous tetrahydrofuran (25 mL) at 0° C. After the addition, the mixture was stirred at 20° C. for 16 h. The reaction mixture was diluted with brine (20 mL) and stirred for 30 min. The mixture was extracted with ethyl acetate (2×50 mL), and washed with brine. The combined organic extract was dried over Na2SO4, and later evaporated on a rotavap. The residue was purified by flash column chromatography on silica gel (230-400 mesh; 24 g) using dichloromethane:methanol:methanol (95:5:0.05) solvent mixture. Yield: 4.02 g (some phosphorus side products were present, used without further purification for subsequent step). 1H NMR (400 MHz, CDCl3): δ 6.70 (m, 2H), 6.63 (m, 1H), 4.02 (m, 4H), 3.96 (m, 1H), 3.75 (m, 2H), 2.91 (t, 2H), 2.58 (t, 2H), 1.41 (m, 9H).

Provenance & Evidence