Multi-step reaction with 13 steps
1: sulfuric acid; water / 20 h / Reflux
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h
3: tetrahydrofuran / 2 h / -78 - 20 °C
4: tetra-N-butylammonium tribromide / methanol; dichloromethane / 3 h / 0 - 20 °C
5: sodium azide / N,N-dimethyl-formamide / 0 - 20 °C
6: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol; water / 5 h / 2068.65 - 3361.55 Torr
7: acetic acid / 4 h / Reflux
8: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h
9: hydrogen fluoride / acetonitrile / 1 h
10: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C
11: sodium azide / N,N-dimethyl-formamide / 1 h / 0 °C
12: hydrogenchloride; hydrogen / platinum(IV) oxide / ethanol / 5 h / 2068.65 - 2327.23 Torr
13: isopropyl alcohol / 24 h / Reflux
With
hydrogenchloride; dmap; sodium azide; di-isopropyl azodicarboxylate; sulfuric acid; hydrogen fluoride; water; hydrogen; tetra-N-butylammonium tribromide; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;