ammonium chloride in ethanol T=0 - 20°C;

sulfuric acid in ethanol T=20°C; acetalization; 12 h;

triethylamine; lithium bromide in tetrahydrofuran T=5 - 25°C;

1: With titanium(IV) isopropylate in ethanol T=20°C; 12 h; 2: With sodium tetrahydroborate in ethanol 12 h;

1: 98 percent / diethyl ether / -75 °C 2: 60 percent / manganese dioxide / toluene / 18 h / Heating 3: 1.) sodium hydride / 1.) ether, RT, 25 min, 2.) ether, ethanol, reflux, 6 h 4: 1.) sodium hydride / 1.) THF, RT, 0.5 h, 2.) THF, reflux, 48 h 5: conc. HCl / acetic acid / 5 h / Heating 6: 71 percent / piperidine / ethanol / 24 h / Heating 7: 81 percent / H2 / Pd/C / tetrahydrofuran / 24 h / 2585.7 Torr / Ambient temperature View Scheme

1.1: sodium tetrahydroborate; methanol / 1 h / 0 °C 2.1: hydrogenchloride; water / tetrahydrofuran / 1 h 3.1: hydrogen bromide / dichloromethane; acetic acid 4.1: sodium azide / N,N-dimethyl-formamide / 1 h / 60 °C 5.1: sodium tetrahydroborate; methanol / 1 h / 0 °C 6.1: triphenylphosphine / tetrahydrofuran / 1 h / 60 °C 6.2: Heating View Scheme

1: 10.0 g / NaBH4 / tetrahydrofuran / 3 h 2: PBr3 / benzene / 0 - 20 °C View Scheme

1: 75 percent / nBuLi / tetrahydrofuran 2: 85 percent / H2SO4; SiO2 / CH2Cl2 / 20 °C View Scheme

1: With lithium aluminium tetrahydride in diethyl ether Reduction; 2 h; Heating; 2: With hydrogenchloride in diethyl ether; water Hydrolysis; 0.0333333 h;

sodium borohydride in methanol; chloroform; ethyl acetate