pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid in dimethyl sulfoxide; benzene Ambient temperature;

1: 88 percent / pyridine / Ambient temperature 2: sodium azide / dimethylsulfoxide / 24 h / 100 °C 3: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature View Scheme

1: 88 percent / pyridine / Ambient temperature 2: sodium azide / dimethylsulfoxide / 24 h / 100 °C 3: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature View Scheme

1.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 10 h / -25 - -15 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme

1: 88 percent / pyridine / Ambient temperature 2: sodium azide / dimethylsulfoxide / 24 h / 100 °C 3: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature View Scheme

Multi-step reaction with 5 steps 1.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere2.2: 10 h / -25 - -15 °C3.1: water; triphenylphosphine / 15 h / 65 °C4.1: triethylamine / dichloromethane / 1 h / 20 °C5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C5.2: 1 h / 20 °C