1: 9.0 g / diborane / tetrahydrofuran / 16 h / 20 °C 2: 6.0 g / 4-(dimethylamino)pyridine; Et3N / CH2Cl2 / 1 h View Scheme

in ethanol

in diethyl ether

borane-THF in tetrahydrofuran T=0°C; 4 h;

1: 2-(3-Bromo-phenyl)-acetic acid With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene T=-78°C; 0.25 h; 2: methyl iodide T=-78 - 20°C;

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / -15 °C / |Inert atmosphere; |Large scale 2.1: N,N-dimethyl-formamide / toluene / 1.5 h / |Inert atmosphere; |Large scale 3.1: potassium carbonate; O,N-dimethyl-hydroxylamine hydrochloride / water / 1.25 h / 30 °C / |Inert atmosphere; |Large scale 3.2: 1.5 h / |Inert atmosphere; |Large scale 4.1: potassium tert-butylate; C62H66Cl2N2P2Ru / toluene; isopropyl alcohol / 0 - 25 °C / |Inert atmosphere; |Glovebox; |Autoclave; |Large scale 4.2: 0 °C / |Glovebox; |Autoclave; |Large scale 5.1: palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 0.92 h / 56 °C / |Inert atmosphere; |Large scale 5.2: 3.25 h / 56 °C / |Inert atmosphere; |Large scale 6.1: triethylamine / toluene / 0.17 h / 20 °C / |Inert atmosphere; |Large scale 7.1: N-ethyl-N,N-diisopropylamine; sodium azide / N,N-dimethyl-formamide / 70 °C / |Inert atmosphere; |Large scale 8.1: triphenylphosphine; water / toluene / 8 h / 70 °C / |Inert atmosphere; |Large scale 9.1: hydrogenchloride / isopropyl alcohol / |Inert atmosphere; |Large scale 10.1: 2,4,6-trichloro-1,3,5-triazine; 4-methyl-morpholine / acetonitrile / 4 h / 50 °C / |Inert atmosphere; |Large scale View Scheme

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane 1 h; Heating;

1: H2SO4 / Heating 2: dimethylformamide / Heating 3: H2; aq. HCl / Pd/C / methanol / 25 °C / 3620.04 Torr 4: Et3N / tetrahydrofuran / 25 °C 5: aq. LiOH / tetrahydrofuran / 25 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / -15 °C / |Inert atmosphere; |Large scale 2.1: N,N-dimethyl-formamide / toluene / 1.5 h / |Inert atmosphere; |Large scale 3.1: potassium carbonate; O,N-dimethyl-hydroxylamine hydrochloride / water / 1.25 h / 30 °C / |Inert atmosphere; |Large scale 3.2: 1.5 h / |Inert atmosphere; |Large scale View Scheme

1: thionyl chloride / toluene / 1 h / Heating 2: 4.9 g / Et3N / CH2Cl2 / 20 °C 3: LiAlH4 / diethyl ether / 0.5 h / 0 °C View Scheme