Triphenylphosphine → HCID 67241724, compound

Participants

Reaction Conditions

Reaction Steps

Diethylazodicarboxylate (40% solution in toluene, 3.3 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 N-Boc-4-piperidinemethanol (1) (1.32 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 (2×30 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; 8 g) using hexane:ethylacetate solvent mixture. Yield: 3.02 g (some phosphorus side products were present, used without further purification for subsequent step). 1H NMR (400 MHz, CDCl3): δ 7.84 (s, 1H), 6.70 (b.s, 1H), 6.67 (m, 2H), 3.74 (d, 2H), 2.91 (t, 2H), 2.70 (b.t, 2H), 2.59 (m, 2H), 1.93 (b.s, 1H), 1.80 (b.d, 2H), 1.44 (m, 9H), 1.24 (m, 2H).

Provenance & Evidence