1: 91 percent / K2CO3 / dimethylformamide; H2O / 24 h / 20 °C 2: 95 percent / NaN3 / methanol; H2O; methyl formate / 46 h / 50 °C 3: 1.) triethylamine, 4-(dimethylamino)pyridine, 2.) H2 / 2.) Pd-C / 1a.) ethyl acetate, 20 deg C, 4h, 1b.) MeOH, 3h, 2.) 68h View Scheme

1: K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature 2: 80 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature 3: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C 4: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2 5: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature View Scheme

1: 91 percent / K2CO3 / dimethylformamide; H2O / 24 h / 20 °C 2: 95 percent / NaN3 / methanol; H2O; methyl formate / 46 h / 50 °C 3: 92 percent / H2 / Pd-C / ethyl acetate / 56 h View Scheme

1: K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature 2: 80 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature 3: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C 4: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2 5: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature 6: 79 percent / acetic acid, zinc / methanol / 0.67 h / 60 °C View Scheme