Multi-step reaction with 13 steps
1.1: sodium tris(acetoxy)borohydride / dichloromethane / 12.25 h / 25 °C / Molecular sieve; Inert atmosphere
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 - 25 °C / Inert atmosphere
2.2: 0.5 h / 0 - 25 °C
3.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 2 h / 0 - 50 °C
4.1: hydroxylamine / water; ethanol / 12 h / 25 °C
5.1: acetic acid / water; methanol / 25 °C
6.1: acetonitrile / 12 h / 25 °C / Molecular sieve
7.1: triethylamine / tetrahydrofuran / 12 h / 50 °C
8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.17 h / 0 °C
9.1: triethylamine; diphenyl phosphoryl azide / 4 h / Reflux
10.1: toluene-4-sulfonic acid / methanol / 3 h / 25 °C
11.1: Jones reagent / acetone / 1 h / 0 °C
12.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 - 25 °C / Inert atmosphere
12.2: 0.5 h / 0 - 25 °C
13.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 °C
With
Jones reagent; diphenyl phosphoryl azide; water; hydroxylamine; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile;
6.1: |Diels-Alder Cycloaddition / 9.1: |Curtius Rearrangement;
DOI:10.1021/ja412298c