hydrogenchloride in benzene

1: 61 percent / triethylamine / CH2Cl2; petroleum ether / -40 - -15 °C 2: 54 percent / LiAlH4, (-)-quinine / diethyl ether; tetrahydrofuran / 24 h / Ambient temperature 3: 72 percent / HCl / benzene View Scheme

1: 54 percent / LiAlH4, (-)-quinine / diethyl ether; tetrahydrofuran / 24 h / Ambient temperature 2: 72 percent / HCl / benzene View Scheme

1: NaN3, methanesulfonic acid / CHCl3 / 0.5 h / 0 °C 2: LiAlH4 / diethyl ether / 3 h / Ambient temperature View Scheme

1: 1) Mg / 1) Et2O, 2) Et2O, reflux, 2.5 h 2: NaBH4 / methanol / 2 h / Ambient temperature View Scheme