n-BuNF in tetrahydrofuran T=-20°C;

1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl-formamide T=20°C; 1 h;

1: NaBH3CN / methanol 2: 33 percent / camphorsulfonic acid / 1,2-dichloro-ethane / 1.) 2 d, 2.) reflux, 1 h 3: 91 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 4: 2.) NH3 / 1.) MeOH, reflux, 4 d, 2.) MeOH, 15 min View Scheme

1: 33 percent / camphorsulfonic acid / 1,2-dichloro-ethane / 1.) 2 d, 2.) reflux, 1 h 2: 91 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 3: 2.) NH3 / 1.) MeOH, reflux, 4 d, 2.) MeOH, 15 min View Scheme

ammonia 1.) MeOH, reflux, 4 d, 2.) MeOH, 15 min; Yield given. Multistep reaction;

1: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 2: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 3: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C View Scheme

1: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 2: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C View Scheme

1: 79 percent / pyridine / CH2Cl2 / 20 h / 20 °C 2: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C 3: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 4: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 5: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C View Scheme

1: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C 2: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 3: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 4: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C View Scheme

1: 61 percent / hydrazoic acid; Ph3P; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C 2: 89 percent / sodiumborohydride / ethanol / 4 h / 20 °C 3: 79 percent / pyridine / CH2Cl2 / 20 h / 20 °C 4: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C 5: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 6: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 7: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C View Scheme