Multi-step reaction with 20 steps
1.1: sodium ethanolate / ethanol / 1.5 h / Cooling with ice
1.2: 3.5 h / 20 °C
2.1: hydrogen / palladium 10% on activated carbon / ethanol; tetrahydrofuran; methanol / 10.5 h / 20 °C / 760.05 Torr
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water / 20 °C / Cooling with ice
4.1: 1,1,3,3-Tetramethyldisiloxane / (Ph3P)2IrCl(CO) / toluene / 3 h / 20 °C
5.1: hydroquinone / acetonitrile / 90 °C
6.1: methyl p-toluene sulfonate / 2 h / 105 °C
7.1: hydrogen / rhodium contaminated with carbon / tetrahydrofuran / 35 h / 20 °C
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
9.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
9.2: Cooling with ice
10.1: triphenylphosphine / dichloromethane / 0.75 h / Cooling with ice
10.2: 1 h / Cooling with ice
10.3: Cooling with ice
11.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C
11.2: 0.33 h / Cooling with ice
12.1: pyridine / methanol / 20 °C
13.1: Iodine monochloride / dichloromethane / 1 h / Cooling with ice
14.1: potassium phosphate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 1 h / 80 °C / Inert atmosphere
15.1: hydrogen / palladium on activated charcoal / tetrahydrofuran; methanol / 5 h / 20 °C / 760.05 Torr
16.1: sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 2 h / 20 °C
17.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
18.1: trifluoroacetic acid / chloroform / 20 °C / Cooling with ice
19.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C / Cooling with ice
20.1: hydrogen bromide; acetic acid / water / 10 - 50 °C
With
pyridine; sodium hypochlorite; sodium chlorite; potassium phosphate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,3,3-Tetramethyldisiloxane; hydrogen bromide; hydrogen; sodium ethanolate; Iodine monochloride; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; hydroquinone; methyl p-toluene sulfonate; triphenylphosphine; trifluoroacetic acid;
bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon; palladium on activated charcoal; rhodium contaminated with carbon; (Ph3P)2IrCl(CO);
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;