1: NaHCO3 / tetrahydrofuran 2: LiAlH4 / tetrahydrofuran / Heating 3: 1) DEAD, Ph3P View Scheme

1: (1R)-3-amino-1-phenyl-1-propanol With sodium hydride in dimethyl sulfoxide T=55°C; 0.5 h; 2: 1-chloro-4-(trifluoromethyl)benzene in dimethyl sulfoxide T=90°C; 1 h;

1.1: NaH / dimethylsulfoxide / 0.5 h / 55 °C 1.2: 90 percent / dimethylsulfoxide / 1 h / 90 °C 2.1: aq. K2CO3 / CH2Cl2 / 0.5 h 3.1: LiAlH4 / tetrahydrofuran / 2 h / 65 °C 4.1: 95 percent / HCl / diethyl ether View Scheme

dimethylsulfide borane complex in tetrahydrofuran 2 h; Heating;

dimethylsulfide borane complex; polymer-supported chiral sulfonamide in tetrahydrofuran Heating;

dimethylsulfide borane complex in tetrahydrofuran Heating;

ammonia; hydrogen; nickel in ethanol T=90°C; p(NH3) = 30 psi and p(H2) = 170 psi; Yield given. Yields of byproduct given;

1: Et3N / CH2Cl2 / 3 h / 20 °C 2: ethanol; H2O / 12 h / 20 °C 3: BH3*Me2S / tetrahydrofuran / 3 h / 65 °C View Scheme

1: ethanol; H2O / 12 h / 20 °C 2: BH3*Me2S / tetrahydrofuran / 3 h / 65 °C View Scheme

1: 99 percent / potassium ferricyanide; potassium carbonate; osmium tetroxide / (DHQ)2PHAL / H2O; 2-methyl-propan-2-ol; toluene / 24 h / 0 °C 2: 99 percent / dibutyltin oxide; triethylamine / CH2Cl2 / 0.75 h / 20 °C 3: 90 percent / ethanol; H2O / 24 h / 20 °C 4: 96 percent / borane dimethyl sulfide complex; methyl sulfide / tetrahydrofuran / 2.5 h / Heating View Scheme