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

Multi-step reaction with 4 steps 1: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature2: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C3: 3M HCl / ethyl acetate / 1 h / Ambient temperature4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature  

Multi-step reaction with 3 steps 1: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C2: 3M HCl / ethyl acetate / 1 h / Ambient temperature3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature  

Multi-step reaction with 11 steps 1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating4: 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 min5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C7: tetrahydrofuran / 20 h / 23 °C8: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C9: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C10: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C11: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C  

Multi-step reaction with 5 steps 1: tetrahydrofuran / 20 h / 23 °C2: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C3: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C4: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C5: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C  

Multi-step reaction with 6 steps 1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C2: tetrahydrofuran / 20 h / 23 °C3: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C4: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C5: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C6: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C  

Multi-step reaction with 10 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating3: 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 min4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C6: tetrahydrofuran / 20 h / 23 °C7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C  

Multi-step reaction with 8 steps 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 min2: 83 percent / acetyl chloride / methanol / 2 h / 50 °C3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C4: tetrahydrofuran / 20 h / 23 °C5: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C6: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C7: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C8: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C  

Multi-step reaction with 7 steps 1: 83 percent / acetyl chloride / methanol / 2 h / 50 °C2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C3: tetrahydrofuran / 20 h / 23 °C4: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C5: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C6: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C7: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C