1: N-carboethoxy-3-fluoro-4-morpholinylaniline With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 3.5 h; Inert atmosphere; 2: (-)-(R)-glycidyl butyrate in tetrahydrofuran; hexane T=-78 - 20°C; 3: With ammonium chloride in tetrahydrofuran; hexane; water T=20°C; 0.5 h; Product distribution / selectivity;

1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: 5 h / 70 °C 4.1: ammonium formate / palladium 10 on activated carbon / methanol / 8 h / 65 °C View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: ammonium hydroxide / isopropyl alcohol; water; tetrahydrofuran / 24 h / 80 - 85 °C / autoclave 4.1: triethylamine / dichloromethane / 5 h / 5 - 20 °C View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 10 h / 0 - 20 °C View Scheme

sodium carbonate in dichloromethane T=5 - 25°C;

1: sodium carbonate / water / 18 h / 20 - 85 °C 2: hydrogen / nickel / ethanolamine; methanol / 20 °C / 3677.86 Torr 3: sodium carbonate / dichloromethane / 5 - 25 °C View Scheme

1: hydrogen / nickel / ethanolamine; methanol / 20 °C / 3677.86 Torr 2: sodium carbonate / dichloromethane / 5 - 25 °C View Scheme