Multi-step reaction with 11 steps
1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h
2: tetrahydrofuran / 2 h / -78 - 20 °C
3: tetra-n-butylammonium tribromide / dichloromethane; methanol / 3 h / 0 - 20 °C
4: sodium azide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
5: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol / 5 h / 3361.55 Torr
6: triethylamine / dichloromethane / 1 h / 0 - 20 °C
7: acetic acid / 4 h / Reflux
8: caesium carbonate / acetonitrile / 2 h
9: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
10: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 0 - 80 °C
11: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
With
hydrogenchloride; dmap; sodium azide; tetra-n-butylammonium tribromide; diphenyl phosphoryl azide; hydrogen; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;