Multi-step reaction with 13 steps
1: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / 36 h / 80 °C / Inert atmosphere
2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
3: dmap / dichloromethane / 48 h / 20 °C
4: tetrabutyl ammonium fluoride; acetic acid / 20 °C / Inert atmosphere
5: di-isopropyl azodicarboxylate; triphenylphosphine; urea / tetrahydrofuran / 0.5 h / 20 °C
6: 5% Pd/C / ethanol / Inert atmosphere
7: sodium hydrogencarbonate / dichloromethane; water / Inert atmosphere
8: dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere
9: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C
10: di-isopropyl azodicarboxylate; triphenylphosphine; urea / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
11: acetic acid; 5% Pd/C / ethanol; toluene / 3 h / Inert atmosphere
12: sodium hydrogencarbonate / dichloromethane; water / Inert atmosphere
13: dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere
With
1H-imidazole; dmap; copper(l) iodide; di-isopropyl azodicarboxylate; 5% Pd/C; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triphenylphosphine; urea; L-proline;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1039/c2cc34791a