phosphorus pentachloride

pyridine in benzene

hydrogenchloride

1: AlCl3 / 2 h / 50 °C 2: 92 percent / H2 / Raney nickel / tetrahydrofuran / 7 h / 3102.9 Torr / Ambient temperature View Scheme

triethylamine in tetrahydrofuran T=0°C; 3 h;

1.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 1.2: 10 - 20 °C 2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2.2: 0 °C / |Reflux 3.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C View Scheme

1.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 1.2: 10 - 20 °C 2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2.2: 0 °C / |Reflux View Scheme

1.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 1.2: 10 - 20 °C 2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2.2: 0 °C / |Reflux 3.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 4.2: 3 h / |Reflux View Scheme

1.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 1.2: 10 - 20 °C 2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 2.2: 0 °C / |Reflux 3.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 4.2: 3 h / |Reflux 5.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 5 h / 60 °C / |Inert atmosphere 2: SnCl2·2H2O; water / ethanol / 12 h / 80 °C / |Inert atmosphere View Scheme