Multi-step reaction with 21 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice
2.1: water; acetic acid / 16 h / 20 °C
3.1: sodium periodate / 1,4-dioxane; water / 1.67 h
4.1: sodium hydroxide; water / tetrahydrofuran / 72 h / 20 °C / Cooling with ice
5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
6.2: 0.5 h / -78 °C
7.1: toluene; diethyl ether / 4 h / -78 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C
9.1: pyridine / 22 h / 0 - 20 °C
10.1: triethylamine / dmap / dichloromethane / 16 h / 0 - 20 °C
11.1: sulfuric acid / 2 h / 20 °C
12.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Reflux
12.2: Cooling with ice; Reflux
13.1: ammonia / methanol / 21 h / 0 °C
14.1: pyridine / 5 h / 0 - 20 °C
15.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 6 h / 20 °C
15.2: 6 h / 80 °C
16.1: pyridine / 6 h / 0 - 20 °C
17.1: N,N-dimethyl-formamide / 16 h / 20 °C
18.1: potassium carbonate / methanol / 16 h / 20 °C
19.1: pyridine
20.1: 1H-imidazole / N,N-dimethyl-formamide
20.2: 45 - 50 °C
21.1: 2,6-dimethylpyridine; pyridine / 45 - 50 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; tetrabutyl ammonium fluoride; ammonia; water; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium hydroxide;
dmap; sulfuric acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;