potassium tert-butylate in tetrahydrofuran 10 h; Ambient temperature;

potassium tert-butylate in dichloromethane T=0 - 20°C; Wittig Olefination; 12 h;

lithium hydroxide; bis(triphenylphosphine)palladium(II)-chloride; diisobutylaluminium hydride 1.) THF, toluene, reflux, 15 h, 2.) THF, H2O, reflux, 6 h; Multistep reaction. Title compound not separated from byproducts;

palladium 10 on activated carbon; hydrogen in ethanol 1 h;

1: 3.77 g / conc. H2SO4 / benzene / 15 h / Heating 2: 68 percent / DBU; p-acetamidobenzenesulfonyl azide / acetonitrile / 2.5 h / 0 - 20 °C 3: 59 percent / Rh2((S)-N-(dodecylbenzenesulfonyl)prolinate)4 / hexane / 16 h / 23 °C 4: DDQ / benzene / 2 h 5: H2 / Pd/C / 2.5 h / 2844.39 Torr 6: aq. HCl / 23 h / Heating 7: ClSO3H / CH2Cl2 / 0.75 h View Scheme

1: 3.77 g / conc. H2SO4 / benzene / 15 h / Heating 2: 68 percent / DBU; p-acetamidobenzenesulfonyl azide / acetonitrile / 2.5 h / 0 - 20 °C 3: 59 percent / Rh2((S)-N-(dodecylbenzenesulfonyl)prolinate)4 / hexane / 16 h / 23 °C 4: DDQ / benzene / 2 h 5: H2 / Pd/C / 2.5 h / 2844.39 Torr 6: aq. HCl / 23 h / Heating 7: ClSO3H / CH2Cl2 / 0.75 h View Scheme

1: 3.77 g / conc. H2SO4 / benzene / 15 h / Heating 2: 68 percent / DBU; p-acetamidobenzenesulfonyl azide / acetonitrile / 2.5 h / 0 - 20 °C 3: 59 percent / Rh2((S)-N-(dodecylbenzenesulfonyl)prolinate)4 / hexane / 16 h / 23 °C 4: DDQ / benzene / 2 h 5: H2 / Pd/C / 2.5 h / 2844.39 Torr 6: aq. HCl / 23 h / Heating 7: ClSO3H / CH2Cl2 / 0.75 h View Scheme