ammonia in ethanol T=120°C; 14 h;

1: 1.) lithium 2,2,6,6-tetramethylpiperidide / 1.) hexane, THF, -70 deg C, 1 h, 2.) -70 deg C, 1.5 h 2: 89 percent / MnO2 / toluene / 1 h / Heating 3: 58 percent / NH3 / ethanol / 14 h / 120 °C View Scheme

1: 89 percent / MnO2 / toluene / 1 h / Heating 2: 58 percent / NH3 / ethanol / 14 h / 120 °C View Scheme

1: 30 percent / triethylamine / dimethylformamide / 24 h / 20 °C 2: 30 percent / CH2Cl2; tetrahydrofuran / 2 h / -78 °C 3: 85 percent / NaOH / methanol / 3 h / Heating View Scheme