hydrogen; acetic acid; palladium on activated charcoal P=2068.6 Torr; 23 h;

water in acetonitrile 24 h; Heating;

1: 93 percent / 10percent aq. NaOH / 1.5 h / Heating 2: SOCl2 / 0.5 h / Heating 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 3 h 4: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h 5: 76 percent / tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C 6: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 7: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme

1: 34 percent / SF4 / CH2Cl2; H2O / 12 h / 95 °C 2: 93 percent / 10percent aq. NaOH / 1.5 h / Heating 3: SOCl2 / 0.5 h / Heating 4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 3 h 5: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h 6: 76 percent / tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C 7: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 8: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme

1: SOCl2 / 0.5 h / Heating 2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 3 h 3: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h 4: 76 percent / tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C 5: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 6: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme

1: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h 2: 76 percent / tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C 3: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 4: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme

1: 76 percent / tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C 2: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 3: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme

1: 82 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C 2: 81 percent / H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr View Scheme

1: 70 percent / DAST / CH2Cl2 / 20 h / -15 °C 2: 66 percent / Bu3SnH; AIBN / benzene / 20 °C 3: 60 percent / H2O / acetonitrile / 24 h / Heating View Scheme

1: 89 percent / aq. HBr / tetrahydrofuran / -30 - 0 °C 2: 70 percent / DAST / CH2Cl2 / 20 h / -15 °C 3: 66 percent / Bu3SnH; AIBN / benzene / 20 °C 4: 60 percent / H2O / acetonitrile / 24 h / Heating View Scheme