1: 13 mg / NH3 / methanol / 24 h / 20 °C 2: 80 percent / trifluoroacetic acid / H2O View Scheme

ammonia in methanol Ambient temperature;

ammonia in methanol 20 h; Ambient temperature; Yield given. Yields of byproduct given;

Multi-step reaction with 8 steps 1: 61 percent / hydrazoic acid; Ph3P; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C2: 89 percent / sodiumborohydride / ethanol / 4 h / 20 °C3: 79 percent / pyridine / CH2Cl2 / 20 h / 20 °C4: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C5: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C6: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C7: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C8: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C