hydrogenchloride; diethyl ether

1.1: NaH / dimethylformamide / 1 h / 0 °C 1.2: 93 percent / dimethylformamide / 2 h / 20 °C 2.1: 87 percent / (R,S)-norephedrine; BH3 / tetrahydrofuran / 48 h / 30 °C 3.1: 82 percent / O3 / methanol / 0.25 h / -78 °C View Scheme