1: With water; lithium hydroxide hydrate in tetrahydrofuran; methanol T=20°C; 2 h; 2: in tetrahydrofuran; methanol; water pH=2; Aqueous phosphate buffer; Product distribution / selectivity;

Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 16 h / 0 °C / Inert atmosphere2.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 1 h / Inert atmosphere3.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere4.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere4.2: 1.67 h / Inert atmosphere4.3: 1 h / Inert atmosphere5.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C6.2: 2 h / -60 - 20 °C7.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere8.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness  

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  

Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere2.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere2.2: 1.67 h / Inert atmosphere2.3: 1 h / Inert atmosphere3.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C4.2: 2 h / -60 - 20 °C5.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere6.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness  

Multi-step reaction with 5 steps 1.1: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere1.2: 1.67 h / Inert atmosphere1.3: 1 h / Inert atmosphere2.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C3.2: 2 h / -60 - 20 °C4.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere5.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness  

Multi-step reaction with 4 steps 1.1: hydrogenchloride; water / N,N-dimethyl-formamide / 2 h / 16 °C / Inert atmosphere2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C2.2: 2 h / -60 - 20 °C3.1: pyridinium p-toluenesulfonate / toluene / 1.6 h / 60 °C / Inert atmosphere4.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / Inert atmosphere; Darkness