Multi-step reaction with 15 steps
1: water; potassium hydroxide / ethanol
2: triethylamine / diethyl ether
3: n-butyllithium / tetrahydrofuran / -78 °C
4: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C
5: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 20 °C
6: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 110 °C
7: chloro-trimethyl-silane / dichloromethane / 20 °C
8: 20% palladium hydroxide on carbon; hydrogen / ethyl acetate
9: 1H-imidazole; zinc azide * 2 pyridine; triphenylphosphine; diethylazodicarboxylate / dichloromethane / 20 °C
10: palladium 10% on activated carbon; hydrogen / ethyl acetate
11: sodium cyanoborohydride / methanol / 20 °C
12: sodium cyanoborohydride / methanol / 20 °C
13: palladium 10% on activated carbon; hydrogen; acetic acid / ethanol
14: triethylamine / dichloromethane / 20 °C
15: hydrogenchloride / methanol / 20 °C
With
1H-imidazole; hydrogenchloride; n-butyllithium; chloro-trimethyl-silane; zinc azide * 2 pyridine; diphenyl phosphoryl azide; 20% palladium hydroxide on carbon; palladium 10% on activated carbon; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; sodium cyanoborohydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; potassium hydroxide; lithium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene;
6: Curtius rearrangement;
DOI:10.1016/j.bmcl.2010.12.060