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