formic acid methyl ester; ammonia; sodium methylate in methanol T=20 - 60°C; P=1500.15 Torr; 4 h;

ammonia in water; ethyl acetate T=10°C; 1 h;

1: thionyl chloride / 8 h / 35 °C 2: ammonia; water / ethyl acetate / 1 h / 10 °C View Scheme

1: sodium hydroxide / water; toluene / 1 h / 40 °C 2: sodium t-butanolate / toluene / 11 h / 60 - 80 °C 3: water; sodium hydroxide / methanol / 1 h / 65 °C 4: thionyl chloride / 8 h / 35 °C 5: ammonia; water / ethyl acetate / 1 h / 10 °C View Scheme

1: sodium t-butanolate / toluene / 11 h / 60 - 80 °C 2: water; sodium hydroxide / methanol / 1 h / 65 °C 3: thionyl chloride / 8 h / 35 °C 4: ammonia; water / ethyl acetate / 1 h / 10 °C View Scheme

1: AlCl3, aluminium chloride / 1.33 h / 50 °C 2: boric acid trimethyl ester; (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1.5 h / 35 - 45 °C 3: sodium hydroxide / water; toluene / 1 h / 40 °C 4: sodium t-butanolate / toluene / 11 h / 60 - 80 °C 5: water; sodium hydroxide / methanol / 1 h / 65 °C 6: thionyl chloride / 8 h / 35 °C 7: ammonia; water / ethyl acetate / 1 h / 10 °C View Scheme

1: boric acid trimethyl ester; (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1.5 h / 35 - 45 °C 2: sodium hydroxide / water; toluene / 1 h / 40 °C 3: sodium t-butanolate / toluene / 11 h / 60 - 80 °C 4: water; sodium hydroxide / methanol / 1 h / 65 °C 5: thionyl chloride / 8 h / 35 °C 6: ammonia; water / ethyl acetate / 1 h / 10 °C View Scheme

1: sodium hypochlorite; water; sodium hydroxide / 14 h / 40 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 3: hydrogenchloride; water / methanol / 1 h View Scheme