N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane 4 h; RefluxInert atmosphere;

phosphorus; thionyl chloride; bromine ueber mehrere Stufen;

1.1: 98 percent / NaN3 / dimethylsulfoxide / 7 h / 40 °C 2.1: H2 / Pd/C / methanol / 3 h 2.2: 97 percent / HCl / diethyl ether; methanol 3.1: 81 percent / Et3N / dimethylformamide / 2 h 4.1: 91 percent / aq. NaOH / tetrahydrofuran / 40 °C View Scheme

sodium hydroxide 0.75 h;

1: LiAlH4 / diethyl ether 2: 5-ethyl-2-methyl-pyridine View Scheme

water; potassium hydroxide T=30°C;