1: (R)-(+)-1-(1-naphthyl)-ethylamine With benzaldehyde T=25 - 30°C; Forster reaction; 2: 1-(3-bromopropyl)-3-(trifluoromethyl)benzene in 1-methyl-pyrrolidin-2-one T=125 - 130°C; Forster reaction; Further stages;

1: With dimethylsulfide borane complex in tetrahydrofuran T=0 - 65°C; 4 h; 2: With methanol T=0°C; 0.5 h; 3: With hydrogenchloride; water T=0 - 90°C; 4 h; Product distribution / selectivity;

1.1: tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: methanesulfonic acid / water; tetrahydrofuran / 65 - 70 °C / Inert atmosphere 3.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0 - 5 °C / Inert atmosphere 4.1: potassium carbonate / acetonitrile / 12 h / 80 - 85 °C / Inert atmosphere 4.2: 50 - 60 °C / pH 0.1 - 0.5 / Inert atmosphere 5.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 5.2: 1 h / 20 °C / Inert atmosphere 6.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: methanesulfonic acid / water; tetrahydrofuran / 65 - 70 °C / Inert atmosphere 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0 - 5 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 12 h / 80 - 85 °C / Inert atmosphere 3.2: 50 - 60 °C / pH 0.1 - 0.5 / Inert atmosphere 4.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: iron acetylacetonate / 1-methyl-pyrrolidin-2-one; tetrahydrofuran / -30 - 0 °C / Inert atmosphere 1.2: 0.25 h / 10 - 35 °C / pH 0 - 1 / Inert atmosphere 2.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: iron acetylacetonate / 1-methyl-pyrrolidin-2-one; tetrahydrofuran / -30 - 0 °C / Inert atmosphere 1.2: 0.25 h / 10 - 35 °C / pH 0 - 1 / Inert atmosphere 2.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: potassium carbonate / acetonitrile / 12 h / 80 - 85 °C / Inert atmosphere 1.2: 50 - 60 °C / pH 0.1 - 0.5 / Inert atmosphere 2.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0 - 5 °C / Inert atmosphere 2.1: potassium carbonate / acetonitrile / 12 h / 80 - 85 °C / Inert atmosphere 2.2: 50 - 60 °C / pH 0.1 - 0.5 / Inert atmosphere 3.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: potassium carbonate / acetonitrile / 12 h / 80 - 85 °C / Inert atmosphere 1.2: 50 - 60 °C / pH 0.1 - 0.5 / Inert atmosphere 2.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere View Scheme

1.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 72 h / 20 °C / 760.05 Torr 2.1: dimethyl sulfoxide; phosphorus pentoxide / dichloromethane / 20 °C / Cooling with ice 2.2: 20 °C / Cooling with ice 3.1: sodium tris(acetoxy)borohydride; methanol / 2 h / 20 °C 4.1: hydrogenchloride / ethyl acetate; water / 1 h / 10 °C / pH 2 View Scheme