Multi-step reaction with 11 steps
1.1: n-butyllithium; N-cyclohexyl-cyclohexanamine / toluene; hexane / 0.33 h / 0 - 15 °C / Inert atmosphere
1.2: 25 °C / Inert atmosphere
2.1: potassium trimethylsilonate / tert-butyl methyl ether; tetrahydrofuran / 2 h / 50 °C / Inert atmosphere
2.2: pH 1
3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h
4.1: tetrahydrofuran / 2 h / -78 - 20 °C
5.1: tetra-n-butylammonium tribromide / dichloromethane; methanol / 3 h / 0 - 20 °C
6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
7.1: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol / 5 h / 3361.55 Torr
8.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
9.1: acetic acid / 4 h / Reflux
10.1: potassium carbonate / acetone / 3 h
11.1: potassium carbonate / acetonitrile / 12 h / 20 °C
With
hydrogenchloride; dmap; n-butyllithium; sodium azide; tetra-n-butylammonium tribromide; potassium trimethylsilonate; hydrogen; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-cyclohexyl-cyclohexanamine;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;