triethylamine in N,N-dimethyl-formamide T=70°C; Inert atmosphereCooling with ice;

sodium hydrogencarbonate in water; xylene T=25 - 30°C; 0.5 h;

1: With 3 A molecular sieve in tetrahydrofuran T=20°C; 60 h; 2: With sodium cyanoborohydride in tetrahydrofuran; ethanol T=23°C; 24 h; Further stages.;

1.1: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1.1: 72 percent / acetic anhydride; pyridine 2.1: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: 167.9 mg / aq. HCl / 2 h / 50 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1.1: 88 percent / p-toluenesulfonic acid / toluene / 15 h / Heating 2.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: 167.9 mg / aq. HCl / 2 h / 50 °C 4.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 4.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1.1: 167.9 mg / aq. HCl / 2 h / 50 °C 2.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 2.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1.1: thionyl chloride / 0.5 h / 0 °C 1.2: 0 °C 2.1: triethylamine / N,N-dimethyl-formamide / 70 °C / Inert atmosphere; Cooling with ice View Scheme

1.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 2.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 2.2: 55 percent / acetic acid / toluene; H2O 3.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme