triethylamine in isopropyl alcohol T=20°C; 2 h; Inert atmosphere;

sodium tetrahydroborate; nickel dichloride in methanol T=0 - 20°C; 15 h;

triethylamine in 1,4-dioxane; water 6 h; Ambient temperature;

in chloroform; water

1: BH3*SMe2 / tetrahydrofuran / Heating 2: satd. NaHCO3 / CHCl3 / 1 h / 20 °C View Scheme

1: N-(tert-butoxycarbonyl)-4-bromophenethylamine With n-butyllithium in diethyl ether; hexane T=0 - 20°C; 1.25 h; 2: carbon dioxide in diethyl ether; hexane T=-78 - 20°C; 1 h; Cooling with acetone-dry ice;

n-butyllithium; carbon dioxide in hexane; water

9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris-(dibenzylideneacetone)dipalladium(0) in N,N-dimethyl-formamide T=100°C; 18 h;

1: 76 percent / ruthenium dioxide hydrate, 10percent aqueous NaIO4 / ethyl acetate / 6 h / Ambient temperature 2: 94 percent / trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: triethylamine; Pd(PPh3)2Cl2; lithium chloride / N,N-dimethyl-formamide / 3 h / 130 °C / |Inert atmosphere; |Microwave irradiation; |Sealed tube 2: hydrogen; palladium 10 on activated carbon / methanol / 3 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / |Inert atmosphere 4: triethylamine / dichloromethane / 3 h / 0 - 20 °C / |Inert atmosphere 5: lithium hydroxide hydrate; water / tetrahydrofuran / 0 - 20 °C View Scheme