1.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 1 h / Inert atmosphere 2.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 3.2: 1.67 h / Inert atmosphere 3.3: 1 h / Inert atmosphere 4.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C 5.2: 2 h / -60 - 20 °C 6.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere 7.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness 8.1: lithium hydroxide hydrate / tetrahydrofuran; water / 16.25 h / 20 °C / Inert atmosphere 8.2: 1 h / Inert atmosphere View Scheme

Multi-step reaction with 7 steps 1.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 1 h / Inert atmosphere2.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere3.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere3.2: 1.67 h / Inert atmosphere3.3: 1 h / Inert atmosphere4.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C5.2: 2 h / -60 - 20 °C6.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere7.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness  

With  sodium tetrahydroborate in  ethanol  

With  tributylphosphine; 1,1'-azodicarbonyl-dipiperidine in  tetrahydrofuran Mitsunobu reaction;   

Multi-step reaction with 2 steps 1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran2: 1H-imidazole / tetrahydrofuran  

Multi-step reaction with 3 steps 1.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 1 h / Inert atmosphere2.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere3.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere3.2: 1.67 h / Inert atmosphere3.3: 1 h / Inert atmosphere