Reaktion #52272

Reaktionsgleichung

Diisopropylazodicarboxylate

3-[5-(2-hydroxy-ethoxy)-indol-1yl]-3-phenyl-propionic acid ethyl ester

N-hydroxyphthalimide

triphenylphosphine

→

title compound

Ausbeute 96.0%

3-{5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

Ausbeute 96.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed under an argon atmosphere at 0° C.
2. 2
   workup.STIRRINGAfter stirring overnight (16 h)
3. 3
   Sonstigethe solvent was removed under vacuum
4. 4
   Sonstigethe crude mixture was purified via column chromatogpraphy

Vorschrift

3-[5-(2-hydroxy-ethoxy)-indol-1yl]-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).

Quelle