Multi-step reaction with 14 steps
1.1: potassium carbonate / acetonitrile / 5 h / 80 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -60 °C
2.2: 1 h / -60 °C
2.3: 2 °C
3.1: triethylamine / tetrahydrofuran / 30 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / 30 °C
5.1: sodium periodate / rhodium(III) chloride hydrate / water; ethyl acetate; acetonitrile / 1 h / 25 °C
5.2: 1 h / 25 °C
6.1: ethanol / 8.5 h / 65 - 80 °C
7.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one; water / 4 h / 20 °C
8.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 16.33 h / 18 - 20 °C
9.1: sodium periodate; water / 16 h / 1.4 - 20 °C
10.1: acetic acid / N,N-dimethyl-formamide; acetonitrile / 0.25 h
10.2: 6.33 h / 20 - 85 °C
11.1: N-ethyl-N,N-diisopropylamine / 1,1'-bis-(diphenylphosphino)ferrocene; palladium(II) trifluoroacetate / dimethyl sulfoxide / 24 h / 80 °C / 2327.23 Torr / Inert atmosphere
12.1: ammonium hydroxide; hydrogen / palladium on activated charcoal / ethanol; water / 2585.81 Torr
13.1: sodium hydroxide / ethanol; water / 14.33 h
14.1: potassium carbonate / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane; water
With
ammonium hydroxide; sodium periodate; N-Bromosuccinimide; water; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane;
1,1'-bis-(diphenylphosphino)ferrocene; palladium(II) trifluoroacetate; rhodium(III) chloride hydrate; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;