Multi-step reaction with 9 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / N,N,N,N,N,N-hexamethylphosphoric triamide / 0.42 h / -78 °C / Inert atmosphere
2.2: 0.25 h / -20 °C / Inert atmosphere
3.1: dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere
5.1: lithium hydroxide monohydrate / water; 1,4-dioxane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
6.2: 12 h / 20 °C / Inert atmosphere
7.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
8.2: 12 h / 20 °C / Inert atmosphere
9.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
With
lithium hydroxide monohydrate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide;
1.1: |Swern Oxidation;
DOI:10.1021/jm3009629