Multi-step reaction with 10 steps
1.1: lithium borohydride; ethanol / tetrahydrofuran / 18 h
2.1: phosphorus tribromide / dichloromethane / 0.67 h / 0 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C
3.2: 16 h / 70 °C
4.1: methanol / 16 h / 65 °C
5.1: 1,4-diaza-bicyclo[2.2.2]octane / tetrahydrofuran / 7 h / 30 °C
6.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / 24 h / Reflux
7.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; ethanol / 3 h / 2250.23 Torr
8.1: trifluoroacetic acid / propyl cyanide / 30 h / 120 °C
9.1: dimethylsulfide borane complex / tetrahydrofuran / 0.5 h / 60 °C
9.2: 8 h / 20 - 60 °C / Inert atmosphere
10.1: boron tribromide / dichloromethane / 3 h / 20 °C / Cooling with ice
With
1,4-diaza-bicyclo[2.2.2]octane; lithium borohydride; ethanol; dimethylsulfide borane complex; hydrogen; boron tribromide; phosphorus tribromide; sodium hydride; triethylamine; trifluoroacetic acid;
palladium 10% on activated carbon; palladium diacetate; tris-(o-tolyl)phosphine;
In
tetrahydrofuran; methanol; propyl cyanide; ethanol; dichloromethane; ethyl acetate; mineral oil;