N-Hydroxyphthalimide → HCID 66819042, compound

Participants

Reaction Steps

3-[5-(2-hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester (0.77 g, 2.10 mmol), N-hydroxyphthalimide (0.40 g, 2.40 mmol) and triphenylphosphine (0.85 g, 3.24 mmol) were dissolved in tetrahydrofuran (5 mL). The mixture was placed under an argon atmosphere at 0° C. and stirred for 10 minutes. Diisopropylazodicarboxylate (0.65 g, 3.24 mmol) was added all at once. After stirring overnight (16 h), the solvent was removed under vacuum, and the crude mixture was purified via column chromatogpraphy to afford the title compound (96% yield). 1H NMR (CDCl3) δ 7.79 (m, 2H), 7.70 (m, 2H), 7.15–7.29 (m, 7H), 7.03 (d, 1H, J=2.3 Hz), 6.69 (dd, 1H, J=2.5, 9.0 Hz), 6.43 (d, 1H, J=3.7 Hz), 5.99 (t, 1H, J=7.7 Hz), 4.56 (m, 2H), 4.34 (m, 2H), 4.02 (c, 2H, J=7.2 Hz), 3.27 (m, 2H), 1.06 (t, 3H, J=7.2 Hz).

Provenance & Evidence