boric acid trimethyl ester; (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; dimethylsulfide borane complex in tetrahydrofuran; toluene T=35 - 45°C; 1.5 h; optical yield given as percent ee;

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 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 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 6: sodium hypochlorite; water; sodium hydroxide / 14 h / 40 °C 7: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 8: hydrogenchloride; water / methanol / 1 h View Scheme

1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride in toluene T=40 - 45°C; 2 h; 2: (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol in toluene T=40 - 60°C; 14.5833 h;

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

sodium hydroxide in water T=40°C; 1 h;