Multi-step reaction with 11 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C
1.2: 3 h / 0 °C
2.1: tetrahydrofuran / 0 °C / Inert atmosphere
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C
7.2: 3 h
8.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C
9.2: 3 h
10.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
11.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C
11.2: 3 h
With
sodium tetrahydroborate; cerium(III) chloride heptahydrate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.bmc.2014.04.011