1: triethylamine; potassium carbonate / dichloromethane / 16 h / 20 °C 2: sodium hydroxide / water; tetrahydrofuran / 16 h / 60 - 65 °C / |Reflux 3: palladium 10 on activated carbon; hydrogen / methanol / 24 h / 20 °C View Scheme

water; acetaldehyde in aq. phosphate buffer; dimethyl sulfoxide Michael Addition; 0.4 h;

3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione in tert-butyl methyl ether T=45°C; Michael condensation; 60 h; optical yield given as percent eeenantioselective reaction;