1: With magnesium; iodine in tetrahydrofuran T=-70 - 70°C; 1 h; 2: With ammonium chloride in tetrahydrofuran T=-5 - 35°C; 3: With hydrogenchloride in water pH=1 - 2;

1: R-(-)-[3-(2-benzyloxy-5-bromophenyl)-3-phenylpropyl]diisopropylamine With ethyl bromide; iodine; magnesium in tetrahydrofuran T=55 - 60°C; 2: carbon dioxide in tetrahydrofuran T=-65 - -60°C; 1 h; 3: With hydrogenchloride in water

1: (R)-3-(2-(benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine, D-tartrate salt With water; sodium hydroxide in dichloromethane T=10 - 20°C; pH=11.5; 0.25 h; 2: With ethyl bromide; iodine; magnesium in tetrahydrofuran T=25 - 55°C; 4 h; Inert atmosphere; 3: carbon dioxide in tetrahydrofuran T=-70 - -10°C; Inert atmosphere;

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 View Scheme

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 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 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 View Scheme

1.1: 25 - 112 °C / Autoclave 2.1: isopropyl alcohol / 14 h / 25 - 80 °C 3.1: sodium hydroxide / water / 0 - 35 °C / pH 9 4.1: magnesium / iodine / tetrahydrofuran / 1 h / -70 - 70 °C 4.2: -5 - 35 °C 4.3: pH 1 - 2 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 View Scheme

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 View Scheme