pyrrolidine in methanol T=0°C; 3 h;

potassium hydroxide in ethanol 12 h; Ambient temperature;

1: 83 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 2: 75 percent / KOH / ethanol / 12 h / Ambient temperature View Scheme

1: 50 percent / Et3N / hexane / 13 h / Ambient temperature 2: 63 percent / aq. NaOH / acetic acid / 10 h / Heating 3: 43 percent / NaN3, conc. H2SO4 / 3 h / 50 °C View Scheme