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 8: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 9: 13 mg / NH3 / methanol / 24 h / 20 °C 10: 80 percent / trifluoroacetic acid / H2O View Scheme

hydrogen azide; triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran; toluene T=20°C; Mitsunobu reaction; 20 h;

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 8: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 9: 13 mg / NH3 / methanol / 24 h / 20 °C View Scheme

1: pyridine; CH2Cl2 / 1 h / -30 °C 2: NaN3 / dimethylformamide / 3 h 3: 91 percent / H2 / 10percent Pd/C / methanol / 14 h 4: 89 percent / trifluoroacetic acid / H2O / 1 h 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

With  pyridine in  dichloromethane T=-40°C;   

Multi-step reaction with 3 steps 1: pyridine; CH2Cl2 / 1 h / -30 °C2: NaN3 / dimethylformamide / 3 h3: 91 percent / H2 / 10percent Pd/C / methanol / 14 h  

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