1: 76 percent / 4-(dimethylamino)pyridine / acetonitrile; CH2Cl2 / 4 h / Ambient temperature 2: 90 percent / bis(1-cyano-1-methylethyl)diazene, tributyltinhydride / toluene / 3 h / 80 °C 3: 29 percent / trimethylsilyl triflate / acetonitrile / 2.5 h / -30 °C 4: 98 percent / NH3 / methanol / 18 h / Ambient temperature View Scheme

diethylamino-sulfur trifluoride in dichloromethane 1 h; Ambient temperature; Yield given. Yields of byproduct given;

1: 52 percent / CrO3/pyridine/Ac2O / CH2Cl2 / 0.5 h / Ambient temperature 2: NaBH4 / ethanol / 0.25 h / 0 °C View Scheme

Multi-step reaction with 2 steps 1: HCl / 0.25 h / Ambient temperature2: 40 percent / pyridine / 4 h / 0 °C  

Multi-step reaction with 3 steps 1: 76 percent / 4-(dimethylamino)pyridine / acetonitrile; CH2Cl2 / 4 h / Ambient temperature2: 90 percent / bis(1-cyano-1-methylethyl)diazene, tributyltinhydride / toluene / 3 h / 80 °C3: 29 percent / trimethylsilyl triflate / acetonitrile / 2.5 h / -30 °C