triethylamine; diethyl dicarbonate in tetrahydrofuran T=0°C; 8 h;

1: 1) N,N'-carbonyldiimidazole / 1) tetrahydrofuran, 30 min, 2) tetrahydrofuran, dimethyl sulfoxide, 4h, room temp. 2: 97 percent / H2 / RuBr2<(R)-binap> / ethanol / 145 h / 20 °C / 76000.1 Torr 3: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 4: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr 5: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 6: 4N HCl / dioxane / 0.5 h / Ambient temperature 7: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 8: 4N HCl / dioxane / 0.5 h / Ambient temperature 9: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 1) n-BuLi / 1) tetrahydrofuran, hexane, -78 deg C, 30 min, 2) tetrahydrofuran, 1h 2: 1) lithium diisopropylamide / 1) tetrahydrofuran, hexane, -78 deg C, 1h, 2) tetrahydrofuran, 5h, -78 up to 0 deg C 3: H2 / 10percent Pd-C / ethanol / Ambient temperature 4: 97 percent / DEPC, triethylamine / tetrahydrofuran / 2 h / 0 °C 5: 83 percent / LiOH*H2O / tetrahydrofuran; H2O / 3 h / 0 °C 6: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr 2: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 3: 4N HCl / dioxane / 0.5 h / Ambient temperature 4: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 5: 4N HCl / dioxane / 0.5 h / Ambient temperature 6: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 1) lithium diisopropylamide / 1) tetrahydrofuran, hexane, -78 deg C, 1h, 2) tetrahydrofuran, 5h, -78 up to 0 deg C 2: H2 / 10percent Pd-C / ethanol / Ambient temperature 3: 97 percent / DEPC, triethylamine / tetrahydrofuran / 2 h / 0 °C 4: 83 percent / LiOH*H2O / tetrahydrofuran; H2O / 3 h / 0 °C 5: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 2: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr 3: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 4: 4N HCl / dioxane / 0.5 h / Ambient temperature 5: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 6: 4N HCl / dioxane / 0.5 h / Ambient temperature 7: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 97 percent / H2 / RuBr2<(R)-binap> / ethanol / 145 h / 20 °C / 76000.1 Torr 2: 96 percent / aq. potassium hydroxide / dioxane / 8 h / 0 °C 3: H2 / 5percent Rh-Al2O3 / ethanol / 16 h / 3040 - 3800 Torr 4: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 5: 4N HCl / dioxane / 0.5 h / Ambient temperature 6: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 7: 4N HCl / dioxane / 0.5 h / Ambient temperature 8: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: H2 / 10percent Pd-C / ethanol / Ambient temperature 2: 97 percent / DEPC, triethylamine / tetrahydrofuran / 2 h / 0 °C 3: 83 percent / LiOH*H2O / tetrahydrofuran; H2O / 3 h / 0 °C 4: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 96 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 2: 4N HCl / dioxane / 0.5 h / Ambient temperature 3: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 4: 4N HCl / dioxane / 0.5 h / Ambient temperature 5: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 91 percent / DEPC, triethylamine / tetrahydrofuran / 6 h / 0 °C 2: 4N HCl / dioxane / 0.5 h / Ambient temperature 3: 71 percent / DEPC, triethylamine / tetrahydrofuran / 8 h / 0 °C View Scheme