triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=0 - 10°C;

potassium hydroxide unter Ausschluss von Licht und anschl. Erwaermen unter 12 Torr auf Siedetemperatur;

1: butan-1-ol; sodium / und Hydrieren des vermutlich als 2-<1,2,3,6-Tetrahydro-<4>pyridyl>-aethanol C7H13NO zu formulierenden Reaktionsprodukts in Essigsaeure an Palladium 2: HBr; water / anschl. mit Alkalilauge View Scheme

1: 100 percent / H2, conc. HCl / Pt/C / H2O / 264 h / Ambient temperature 2: 98 percent / 4M NaOH / Ambient temperature 3: (COCl)2, DMSO, Et3N / tetrahydrofuran / 0.5 h / -35 - 20 °C 4: 1.) nBuLi / 1.) THF, hexane, room temperature, 30 min, 2.) -78 deg C -> room temperature, 1 h 5: I2 / CHCl3 / 192 h / Irradiation 6: 72 percent / Ad-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 7 h, 2.) room temperature, 17 h 7: 1.) CH3C(OCH3)3, TMSCL, 2.) K2CO3 / 1.) CH2Cl2, room temperature, 3 h, 2.) MeOH, room temperature, 1 h View Scheme

1: 85 percent / 40percent aqueous NaOH / 1.5 h / 15 °C 2: 84 percent / acetone / 24 h / 25 °C View Scheme

sodium hydroxide T=15°C; 1.5 h;

1: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 2: aq. H2O2; MeReO3 / CH2Cl2 / 1 h / 20 °C 3: dimethylcarbamoyl chloride / CH2Cl2 / 23 h / 20 °C 4: TBAF / tetrahydrofuran / 48 h / 20 °C View Scheme

diethylamino-sulfur trifluoride in dichloromethane T=10°C; 2.5 h;

1: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 2: aq. H2O2; MeReO3 / CH2Cl2 / 1 h / 20 °C 3: dimethylcarbamoyl chloride / CH2Cl2 / 23 h / 20 °C 4: 6 N aq. HCl / 24 h / Heating View Scheme

triphenylphosphine; N-ethyl-N,N-diisopropylamine in tetrahydrofuran