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in water T=0°C; 1.5 h;

ethanol

1.1: (R)-4-tBu-2-[2-(2Bp-Ph-phosphanyl)-Cp]4,5diH-oxazole*Mn(CO)3; [(η3-C3H5)PdCl]2 / tetrahydrofuran / 0.25 h / 0 °C 1.2: 98 percent / tetrahydrofuran / 0.58 h / 0 °C 2.1: 91 percent / aq. NaOH / 4 h / Heating 3.1: 84 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Heating 4.1: 88 percent / tetrabromomethane; triphenylphosphane / CH2Cl2 / 0 - 20 °C 5.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3.5 h / Heating 5.2: 58 percent / Li2CuCl4 / tetrahydrofuran / -20 °C View Scheme

1: 1) magnesium / 1) THF, -12 to -7 deg C, 1 h, 2) to room temperature, overnight 2: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 3: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight 4: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 5: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 6: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 7: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 8: 82 percent / dimethylformamide / Ambient temperature; overnight 9: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 10: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: 1) magnesium / 1) THF, -12 to -7 deg C, 1 h, 2) to room temperature, overnight 2: 68 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 0 °C 3: 98 percent / triethylamine, DMAP / CH2Cl2 / 0 deg C to room temperature, overnight 4: 1) dibromodimethylhydantoin, 2) potassium carbonate / 1) acetone, water, 0 deg C, 2) methanol, room temperature, overnight 5: 84 percent / sodium azide, ammonium chloride / aq. ethanol / 72 h / 100 °C 6: 21 percent / diethylaminosulphur trifluoride / CH2Cl2 / 0.17 h / 0 °C 7: 99 percent / H2 / Lindlar / ethanol / 3 h / 760 Torr / Ambient temperature 8: 82 percent / dimethylformamide / Ambient temperature; overnight 9: 89 percent / p-toluenesulphonic acid / CH2Cl2; methanol / 3 h / Ambient temperature 10: 88 percent / aq. hydrochloric acid / 0.5 h / Heating View Scheme

1: cold aqueous NaHCO3 2: concentrated aqueous HCl 3: platinum; ethyl acetate / Hydrogenation View Scheme

1: xylene 2: sodium ethylate; ethanol / 180 °C / Erhitzen des Reaktionsprodukts mit Acetanhydrid View Scheme

diethyl ether

1: alcohol 2: durch Verseifung 3: bei der Destillation im Vakuum View Scheme