1: NaOH / methanol; H2O / 2 h / Heating 2: 43 percent / acetic anhydride / 4 h / 90 °C 3: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d View Scheme

hydrogenchloride; water; toluene-4-sulfonic acid 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d; Yield given. Multistep reaction;

1: 43 percent / acetic anhydride / 4 h / 90 °C 2: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d View Scheme

1: (S)-(-)-2-hydroxy-1,2,2-triphenyl-ethyl acetate With lithium diisopropyl amide in tetrahydrofuran; ethylene glycol dimethyl ether T=-10 - 0°C; 0.5 h; 2: 5-(4-fluorophenyl)-2-(1-methylethyl)-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide in tetrahydrofuran; ethylene glycol dimethyl ether T=-78°C; 0.5 h; 3: With methanol; water 3 h; Heating / reflux;

1: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h 2: 1.) tributylborane, sodium borohydride, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, a) RT, b) 0 deg C, 3 h, 2.) RT 3: toluene / 6 h / Heating View Scheme

1.1: (S)-2-(N-3-tert-butylsalicylidene)amino-3-methyl-1-butanol / dichloromethane / 1 h / |Inert atmosphere 1.2: 48 h / -40 °C / |Inert atmosphere 1.3: 1 h / 20 °C 2.1: diethyl methoxy borane; sodium tetrahydroborate / tetrahydrofuran / 2 h / -78 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: sodium hydroxide / water; methanol / 1 h / 50 °C 3.2: 1 h / 20 °C View Scheme