1: 91 percent / triethylamine; 4-(dimethylamino)pyridine / CHCl3 / 24 h 2: 89 percent / acetyl chloride; benzyltriethylammonium nitrite / CH2Cl2 / 0.08 h / -5 - 0 °C 3: ammonia / methanol; CH2Cl2 / 7 h / 80 °C View Scheme

triphenylphosphine; diethylazodicarboxylate 1) dioxane, RT, 2) dioxane, RT; Yield givenMultistep reaction;

N-bromoacetamide in chloroform 2 h;

1: 1.) PPh3, 2.) DEAD / 1.) dioxane, 80 deg C, 30 min, 2.) dioxane, 60 deg C, 2 h 2: NH3 / methanol / 15 h / Ambient temperature 3: HF, pyridine, t-BuONO / 2 h / -30 °C 4: 2.5 g / pyridine / 15 h / Ambient temperature 5: 84 percent / dimethylformamide / 24 h / Ambient temperature 6: 73 percent / DBU, pyridine / 15 h / Ambient temperature View Scheme

1: PPh3, ethyl azodicarboxylate / dioxane / 8 h / 50 °C 2: conc. NH3 / dioxane; methanol / 20 h / Ambient temperature 3: 91 percent / 3-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 4: pyridine / acetonitrile / 0.5 h 5: pyridine / acetonitrile / 0.58 h 6: NH4F / methanol / 0.05 h 7: 66 percent / pyridine / 16 h 8: 1M DBU / acetonitrile / 0 h View Scheme

1: 95 percent / pyridine; EtN(iPr)2 / 20 °C 2: Ph3P; I2; EtN(iPr)2 / toluene / 2 h / 80 °C 3: AcOH; H2O / dioxane / 20 °C 4: 407 mg / NH3 / methanol / 3 h / 70 °C 5: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme