Multi-step reaction with 14 steps
1: sodium hydride / tetrahydrofuran / 20 °C
2: palladium 10% on activated carbon; hydrogen / ethanol
3: water; potassium hydroxide / ethanol / 20 °C
4: triethylamine / diethyl ether / 20 °C
5: n-butyllithium / tetrahydrofuran / -78 °C
6: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C
7: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 20 °C
8: hydrogenchloride / tetrahydrofuran; water / 20 °C
9: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 110 °C
10: chloro-trimethyl-silane / dichloromethane / 20 °C
11: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C
12: water; sodium hydroxide / ethanol / 20 °C
13: ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
14: trifluoroacetic acid / dichloromethane / 20 °C
With
hydrogenchloride; n-butyllithium; chloro-trimethyl-silane; diphenyl phosphoryl azide; palladium 10% on activated carbon; ammonia; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; sodium tris(acetoxy)borohydride; sodium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium hydroxide; sodium hydroxide; lithium hydroxide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
9: Curtius rearrangement;
DOI:10.1016/j.bmcl.2010.12.060