sodium hydroxide; acetic anhydride in methanol; diethyl ether; benzene

acetic anhydride T=130 - 135°C; 2 - 3 h;

1: 85 percent / imidazole / CH2Cl2 / 6 h / Ambient temperature 2: NaOH / methanol / 11.5 h / Ambient temperature 3: acetic anhydride / benzene / 1.33 h / Heating View Scheme

1: 85 percent / imidazole / CH2Cl2 / 6 h / Ambient temperature 2: NaOH / methanol / 11.5 h / Ambient temperature 3: acetic anhydride / benzene / 1.33 h / Heating View Scheme

sodium T=0°C; 1 h;

methanol; C42H47F6N5O3 T=20°C;

1: 1.) Et3N / 1.) DMAP, -30 deg C 2: HF / acetonitrile 3: 43 percent / tetrahydrofuran / 0.17 h / -78 °C 4: C3H4N2 5: H2 / Pd-C 7: LiCl/DBU / acetonitrile 8: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C 9: HF / acetonitrile 10: NaBH4 / 0.5 h / -15 °C 11: 70 percent / p-TsOH / benzene View Scheme

N-((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-3,5-bis(trifluoromethyl)benzenesulfonamide in tert-butyl methyl ether T=-20°C; 28 h; optical yield given as percent eeenantioselective reaction;

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 View Scheme

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