1.1: potassium carbonate; sodium iodide / acetone / Reflux 2.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 2.2: 3 h / 10 °C 3.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 4.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 5.1: isopropyl alcohol / 15 h / 25 - 86 °C 6.1: sodium hydroxide / water 7.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 7.2: 1 h / -65 - -60 °C 8.1: thionyl chloride / 10 °C / Reflux 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 10.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 2.1: isopropyl alcohol / 15 h / 25 - 86 °C 3.1: sodium hydroxide / water 4.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 4.2: 1 h / -65 - -60 °C 5.1: thionyl chloride / 10 °C / Reflux 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 7.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 1.2: 3 h / 10 °C 2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 3.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 4.1: isopropyl alcohol / 15 h / 25 - 86 °C 5.1: sodium hydroxide / water 6.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 6.2: 1 h / -65 - -60 °C 7.1: thionyl chloride / 10 °C / Reflux 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 9.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: methanesulfonic acid / 50 - 55 °C / Inert atmosphere 2.1: ethanol / 20 - 60 °C / Inert atmosphere 3.1: sodium hydrogencarbonate / ethyl acetate / Inert atmosphere 3.2: 3.5 h / 20 °C 3.3: 0.5 h / -10 - 20 °C View Scheme

1: With lithium aluminium tetrahydride in tetrahydrofuran 2 h; 2: With water; sodium hydrogencarbonate in tetrahydrofuran T=0°C; Product distribution / selectivity;

1.1: sulfuric acid / 120 - 125 °C 2.1: potassium carbonate; sodium iodide / acetone / Reflux 3.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 3.2: 3 h / 10 °C 4.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 5.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 6.1: isopropyl alcohol / 15 h / 25 - 86 °C 7.1: sodium hydroxide / water 8.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 8.2: 1 h / -65 - -60 °C 9.1: thionyl chloride / 10 °C / Reflux 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 11.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1: thionyl chloride / 10 °C / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 3: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 1.2: 1 h / -65 - -60 °C 2.1: thionyl chloride / 10 °C / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 4.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: 1-methyl-piperazine / toluene / Heating 1.2: 5 h / Reflux 2.1: 5 Pd(II)/C(eggshell); hydrogen / 1,1-dimethylpropan-1-ol / 80 °C / 5171.62 Torr 3.1: 1,1-dimethylpropan-1-ol / 70 °C / Resolution of racemate; Large scale reaction 4.1: potassium carbonate / water; toluene / 6 h / 50 °C View Scheme

1.1: sulfuric acid / 4 h / 25 - 125 °C 2.1: potassium carbonate; sodium iodide / acetone / 2 h / 25 - 60 °C 3.1: AlCl3, aluminium chloride; sodium tetrahydroborate / ethylene glycol dimethyl ether / 3.5 h / 0 - 10 °C 3.2: 0 - 5 °C 4.1: triethylamine / dichloromethane / 0.5 h / 20 - 30 °C 5.1: 25 - 112 °C / Autoclave 6.1: isopropyl alcohol / 14 h / 25 - 80 °C 7.1: sodium hydroxide / water / 0 - 35 °C / pH 9 8.1: magnesium / iodine / tetrahydrofuran / 1 h / -70 - 70 °C 8.2: -5 - 35 °C 8.3: pH 1 - 2 9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 0 - 5 °C 10.1: hydrogen / 5 palladium on charcoal / methanol / 2 h / 25 - 35 °C / Autoclave 10.2: 25 - 35 °C View Scheme