1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile 4 h; Ambient temperature;

1: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 2: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 3: 3M HCl / ethyl acetate / 1 h / Ambient temperature 4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 5: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

1: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 2: 3M HCl / ethyl acetate / 1 h / Ambient temperature 3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 4: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 7: tetrahydrofuran / 20 h / 23 °C 8: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 9: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 10: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 11: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 12: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

1: tetrahydrofuran / 20 h / 23 °C 2: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 3: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 4: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 5: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 6: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 2: tetrahydrofuran / 20 h / 23 °C 3: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 4: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 5: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 6: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 7: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 6: tetrahydrofuran / 20 h / 23 °C 7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 11: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

1: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 2: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 4: tetrahydrofuran / 20 h / 23 °C 5: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 6: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 7: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 8: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 9: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

1: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 3: tetrahydrofuran / 20 h / 23 °C 4: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 5: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 6: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 7: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 8: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

1: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 2: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 3: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 4: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 5: tetrahydrofuran / 20 h / 23 °C 6: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 7: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 8: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 9: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 10: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme