lithium aluminium tetrahydride in diethyl ether T=0°C; 1 h;

caesium carbonate in ethyl acetate; N,N-dimethyl-formamide

C36H50Cl2N3OPPd; potassium carbonate; 2-oxo-3,3-dimethyl-butanoic acid in N,N-dimethyl acetamide T=110°C; 12 h; Inert atmosphereSchlenk technique; regioselective reaction;

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; Cooling with ice;

1: 88 percent / benzyltrimethylammonium bromide; Pd(OAc)2; aq. K2CO3 / 3 h 2: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C View Scheme

1: 85 percent / Pd(PPh3)4 / toluene / 16 h / Heating 2: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C View Scheme

1: 88 percent / benzyltrimethylammonium bromide; Pd(OAc)2; aq. K2CO3 / 3 h 2: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C View Scheme

bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide T=80°C; Yield given;

1: 92 percent / IBCF, NMM, NaBH4 / tetrahydrofuran / 0 °C 2: PdCl2(PPh3)2, CsCO3 / dimethylformamide / 80 °C View Scheme

1.1: thionyl chloride; benzotriazol-1-ol / dichloromethane 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere 2.2: 20 - 60 °C 3.1: water; sodium hydroxide / methanol / 20 h / 20 °C 4.1: toluene / 2 h / Reflux 5.1: hydrogenchloride / 1,4-dioxane / 4 h / Reflux 6.1: phenylalanine ammonia-lyase / 168 h / 30 °C / pH 8.8 / aq. buffer; Inert atmosphere; Enzymatic reaction View Scheme