1: (2R,4S)-2-ethyl-4-methoxycarbonylamino-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester With potassium hydride in tetrahydrofuran T=20°C; 0.25 h; Inert atmosphere; 2: 3,5-bis-(trifluoromethyl)benzyl bromide in tetrahydrofuran T=20°C; 4 h; Inert atmosphere;

pyridine; hydrogenchloride in dichloromethane

pyridine in dichloromethane T=-10 - 0°C; 20 h; Inert atmosphereLarge scale;

pyridine in tert-butyl alcohol T=35°C; Inert atmosphere;

1: (S)-P-Phos / Pd(OTf)2*2H2O / toluene / 36 h / 50 °C 2: 92 percent / sodium borohydride; MgCl2*6H2O / ethanol; H2O / -10 - 0 °C 3: 82 percent / pyridine / CH2Cl2 / 2.5 h / 0 - 20 °C View Scheme

1: (S)-P-Phos / Pd(OTf)2*2H2O / toluene / 36 h / 50 °C 2: 92 percent / sodium borohydride; MgCl2*6H2O / ethanol; H2O / -10 - 0 °C 3: 82 percent / pyridine / CH2Cl2 / 2.5 h / 0 - 20 °C View Scheme

1: 92 percent / sodium borohydride; MgCl2*6H2O / ethanol; H2O / -10 - 0 °C 2: 82 percent / pyridine / CH2Cl2 / 2.5 h / 0 - 20 °C View Scheme

1.1: caesium carbonate / toluene / 1 h / 20 °C / |Inert atmosphere 1.2: 16 h / 20 - 79 °C / |Inert atmosphere 2.1: sulfuric acid; water / 17 h / 35 °C / |Inert atmosphere; |Large scale 3.1: lithium tert-butylate / tetrahydrofuran; di-isopropyl ether / 0.17 h / 2 - 5 °C / |Inert atmosphere; |Large scale 4.1: sodium tetrahydroborate / toluene; ethanol; water / 0.33 h / 20 °C / |Inert atmosphere; |Large scale 4.2: 0.75 h / -10 - 0 °C / |Inert atmosphere; |Large scale 5.1: pyridine / dichloromethane / 20 h / -10 - 0 °C / |Inert atmosphere; |Large scale View Scheme

1.1: tetrahydrofuran / 6.5 h / 40 - 65 °C 2.1: sodium carbonate / dichloromethane / 2 h / |Inert atmosphere 3.1: caesium carbonate / toluene / 1 h / 20 °C / |Inert atmosphere 3.2: 16 h / 20 - 79 °C / |Inert atmosphere 4.1: sulfuric acid; water / 17 h / 35 °C / |Inert atmosphere; |Large scale 5.1: lithium tert-butylate / tetrahydrofuran; di-isopropyl ether / 0.17 h / 2 - 5 °C / |Inert atmosphere; |Large scale 6.1: sodium tetrahydroborate / toluene; ethanol; water / 0.33 h / 20 °C / |Inert atmosphere; |Large scale 6.2: 0.75 h / -10 - 0 °C / |Inert atmosphere; |Large scale 7.1: pyridine / dichloromethane / 20 h / -10 - 0 °C / |Inert atmosphere; |Large scale View Scheme

1.1: sodium carbonate / dichloromethane / 2 h / |Inert atmosphere 2.1: caesium carbonate / toluene / 1 h / 20 °C / |Inert atmosphere 2.2: 16 h / 20 - 79 °C / |Inert atmosphere 3.1: sulfuric acid; water / 17 h / 35 °C / |Inert atmosphere; |Large scale 4.1: lithium tert-butylate / tetrahydrofuran; di-isopropyl ether / 0.17 h / 2 - 5 °C / |Inert atmosphere; |Large scale 5.1: sodium tetrahydroborate / toluene; ethanol; water / 0.33 h / 20 °C / |Inert atmosphere; |Large scale 5.2: 0.75 h / -10 - 0 °C / |Inert atmosphere; |Large scale 6.1: pyridine / dichloromethane / 20 h / -10 - 0 °C / |Inert atmosphere; |Large scale View Scheme