Multi-step reaction with 13 steps
1: sulfuric acid; acetic acid / 3.5 h
2: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C / Inert atmosphere; Reflux
3: methylamine / water; tetrahydrofuran / 0.5 h / 20 °C
4: dmap; trifluoromethane sulfonyl chloride / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with ice
5: sodium hydroxide; water / tetrahydrofuran / 1.5 h / 20 °C
6: pyridine / dichloromethane / 1 h / Inert atmosphere; Cooling with ice
7: sodium azide / N,N-dimethyl-formamide / 48 h / Inert atmosphere
8: water; tributylphosphine / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere
9: pyridine / dichloromethane / 0.5 h / Inert atmosphere
10: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 3.5 h / Inert atmosphere; Reflux
11: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
12: dipyridinium dichromate / N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere; Molecular sieve
13: water; ammonia / methanol / 19 h / 20 °C
With
pyridine; dmap; dipyridinium dichromate; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; tributylphosphine; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; ammonia; water; acetic acid; methylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;