hydrogen fluoride in acetonitrile T=0 - 20°C; 1.5 h;

1: in acetonitrile 20 h; Reflux; 2: With hydrogen fluoride in acetonitrile T=20°C; 3 h; Cooling with ice; 3: With sodium hydrogencarbonate in dichloromethane; water; acetonitrile

1.1: n-butyllithium; triphenylemethane; N-pyrrolidinylnorephedrine / toluene; hexane; tetrahydrofuran / 2 h / -78 °C 1.2: 3 h 2.1: hydrogen / palladium 10 on activated carbon / ethyl acetate 3.1: sodium methylate / 3 h / 0 - 5 °C / Cooling with ice 3.3: pH 6.5 4.1: triethylamine / hexane / 3 h / -40 °C 5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 °C 5.2: 3 h / -78 °C 6.1: acetonitrile / 20 h / Reflux 6.2: 3 h / 20 °C / Cooling with ice View Scheme

1: 71.3 percent / acetonitrile / 14 h / Heating 2: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 86.7 percent / piperidine, AcOH / benzene / Heating 2: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 3: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 4: 46.9 g / ethanol / 1 h / Ambient temperature 5: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 6: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 7: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 8: 71.3 percent / acetonitrile / 14 h / Heating 9: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 2: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 3: 46.9 g / ethanol / 1 h / Ambient temperature 4: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 5: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 6: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 7: 71.3 percent / acetonitrile / 14 h / Heating 8: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 4: 71.3 percent / acetonitrile / 14 h / Heating 5: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 2: 46.9 g / ethanol / 1 h / Ambient temperature 3: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 4: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 5: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 6: 71.3 percent / acetonitrile / 14 h / Heating 7: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 2: 71.3 percent / acetonitrile / 14 h / Heating 3: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 3: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 4: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 5: 71.3 percent / acetonitrile / 14 h / Heating 6: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme