N-bromosuccinmide; silver nitrate in acetone T=20°C; 2 h;

1.1: ethylmagnesium bromide / diethyl ether / 6 h / Inert atmosphere; Reflux 1.2: 1.5 h / -30 °C / Inert atmosphere 2.1: (S)-Alpine borane / 16 h / 20 °C / Inert atmosphere; Neat (no solvent) 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Reflux 4.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 5.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 6.1: acetic acid / tetrahydrofuran; water / 24 h / 70 °C 7.1: Jone's reagent / acetone / 4 h / 0 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 0 °C / Inert atmosphere 9.1: toluene-4-sulfonic acid / methanol; dichloromethane / 2.5 h / 20 °C / Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere View Scheme

1: 45 percent / 2-aminopropane, cuprous chloride, NH2OH*HCl / ethanol / 2 h / Ambient temperature 2: 85 percent / potassium hydroxide / benzene / 5 h / Heating View Scheme

N,N,N',N,-tetramethylethylenediamine; oxygen; copper(l) chloride in tetrahydrofuran 24 h; Ambient temperature;

copper(l) iodide; N,N,N',N,-tetramethylethylenediamine; oxygen in ethylene glycol dimethyl ether T=55°C; Hay coupling;

1: (i) LiNH2, liq. NH3, THF, (ii) /BRN= 1756103/, THF 2: (hydrogenation) View Scheme

1: 78 percent / n-BuLi / hexamethylphosphoric acid triamide 2: ethylenediamine, NaH / 45 - 55 °C View Scheme

potassium carbonate T=180°C;