sodium hydride in paraffin oil T=90°C;

1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 20 °C 2: AlCl3, aluminium chloride / dichloromethane / 2 h / 20 °C 3: sodium hydride / paraffin oil / 90 °C View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 2: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere View Scheme

1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 2: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 3: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 5: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 6: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 7: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 8: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: 5,6-Dimethoxy-1-oxoindane-2-carboxylic acid methyl ester With potassium carbonate in N,N-dimethyl-formamide T=20°C; 0.5 h; 2: 4-iodomethyl-piperidine-1-carboxylic acid tert-butyl ester in DMF (N,N-dimethyl-formamide) T=20 - 50°C; 5.5 h;