Allyl iodide → (4S)-3-{(2S)-2-[(5-methylindolyl)methyl]pent-4-enoyl}-4-phenyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of NaHMDS 1 M in THF (36.40 mL, 36.40 mmol) was added dropwise a solution of 8 (11.51 g, 33.04 mmol) in THF (180 mL) at −78° C. under argon. The solution was stirred at −78° C. (2 h), then allyl iodide (6.66 g, 39.65 mmol) in THF (70 mL) was added and the mixture was stirred for an additional 2 h at −78° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched by the addition of ice-cold saturated NH4Cl solution (200 mL), extracted with EtOAc, washed with brine and dried (Na2SO4). Evaporation provided a residue, which was purified by silica gel flash chromatography to provide 9 as colorless oil. (7.82 g, 61% yield). H NMR (d6-DMSO) δ 7.37-7.21 (m, 8H), 6.97 (dd, 1H, J=1.5 Hz & 8.5 Hz), 6.31 (dd, 1H, J=0.8 Hz & 3.1 Hz), 5.56 (m, 1H), 5.34 (dd, 1H, J=3.8 Hz & 8.5 Hz), 4.94-4.90 (m, 2H), 4.50 (t, 1H, J=8.7), 4.46-4.38 (m, 2H), 4.17 (m, 1H), 4.11 (dd, 1H, J=3.5 Hz & 8.8 Hz), 2.37 (s, 3H), 2.32 (m, 1H), 2.17 (m, 1H). FABMS (+Ve) m/z 388 [M+], 389 [MH+]. Anal. Calcd for C24H24N2O3 C, 74.21; H, 6.23; N, 7.21. Found C, 74.29; H, 6.22; N, 7.20.

Provenance & Evidence