N,N-diisopropylamine tetrazolide in dichloromethane Ambient temperature;

N-ethyl-N,N-diisopropylamine in tetrahydrofuran 4.5 h;

1: 1.) cc. H2SO4, 2.) NaH / 1.) 4 deg C, 16 h, 2.) DMF, 40 deg C 2: 125.9 g / SnCl4 / CH2Cl2 / 35 h / 3 °C 3: pyridine, 4-(dimethylamino)-pyridine / 17 h 4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 5: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 6: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 7: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 8: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 9: 30percent NaOMe / methanol / Ambient temperature; pH 11 10: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 11: pyridine / 5 h / Ambient temperature 12: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: pyridine, 4-(dimethylamino)-pyridine / 17 h 2: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 3: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 4: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 5: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 6: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 7: 30percent NaOMe / methanol / Ambient temperature; pH 11 8: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 9: pyridine / 5 h / Ambient temperature 10: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 2: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 3: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 4: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 5: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 6: 30percent NaOMe / methanol / Ambient temperature; pH 11 7: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 8: pyridine / 5 h / Ambient temperature 9: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: 125.9 g / SnCl4 / CH2Cl2 / 35 h / 3 °C 2: pyridine, 4-(dimethylamino)-pyridine / 17 h 3: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 4: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 5: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 6: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 7: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 8: 30percent NaOMe / methanol / Ambient temperature; pH 11 9: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 10: pyridine / 5 h / Ambient temperature 11: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 2: pyridine / 5 h / Ambient temperature 3: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 2: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 3: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 4: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 5: 30percent NaOMe / methanol / Ambient temperature; pH 11 6: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 7: pyridine / 5 h / Ambient temperature 8: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 2: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 3: 30percent NaOMe / methanol / Ambient temperature; pH 11 4: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 5: pyridine / 5 h / Ambient temperature 6: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme

1: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 2: 30percent NaOMe / methanol / Ambient temperature; pH 11 3: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 4: pyridine / 5 h / Ambient temperature 5: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme