Multi-step reaction with 12 steps
1.1: dichloromethane; methanol; diethyl ether / 0.25 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
2.2: 1.5 h / 20 °C / Inert atmosphere
3.1: methanol; lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 20 °C
4.1: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 20 °C / Inert atmosphere
5.1: methanol; lithium hydroxide monohydrate / tetrahydrofuran; water / 0.5 h / 20 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere
7.1: triethylamine; dmap / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
8.1: cyclohexa-1,4-diene; N-methylcarbazole / tetrahydrofuran; water / 18 h / Inert atmosphere; UV-irradiation
9.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / acetonitrile / 2 h / Inert atmosphere
10.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
11.1: sodium azide / N,N-dimethyl-formamide / 50 °C
12.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 4 h / 0 °C
With
methanol; dmap; sodium azide; N-methylcarbazole; lithium hydroxide monohydrate; cyclohexa-1,4-diene; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.201400046