Multi-step reaction with 10 steps
1.1: diethyl ether
2.1: nitric acid; acetic anhydride / isopropyl alcohol / -40 °C
3.1: triethylamine / ethyl acetate / 4 h / 20 °C
4.1: sodium tetrahydroborate; 5%-palladium/activated carbon / ethyl acetate; ethanol; water / 0 - 20 °C
5.1: dmap / 7 h
5.2: DIPC / 24 h
6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h
7.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h
7.2: 24 h
8.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 168 h
9.1: N,N,N',N'-tetramethylformamidium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C
10.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C
With
dmap; sodium tetrahydroborate; lithium hydroxide monohydrate; 5%-palladium/activated carbon; N,N,N',N'-tetramethylformamidium hexafluorophosphate; water; nitric acid; acetic anhydride; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo302238u