1: 96 percent / K2CO3 / acetone; dimethylformamide / 64 h / Ambient temperature 2: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C 3: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature 4: 69 percent / hydrogen / 84.5percent PtO2 / ethanol / 2.75 h / 2327.2 Torr 5: 111 g / pyridine / 1.42 h / 5 °C 6: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride 7: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C 8: 81 percent / hydrogen / 84.5percent PtO2 / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr 9: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h 10: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating 11: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene 12: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 13: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 14: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 83 percent / hydrogen / PtO2 / ethanol; tetrahydrofuran / 3.25 h / 724.01 Torr 2: 48 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 48 h 3: 78 percent / aq. NaOH / methanol; dimethylformamide / 0.5 h / 40 - 50 °C 4: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 5: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 6: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C 2: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature 3: 69 percent / hydrogen / 84.5percent PtO2 / ethanol / 2.75 h / 2327.2 Torr 4: 111 g / pyridine / 1.42 h / 5 °C 5: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride 6: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C 7: 81 percent / hydrogen / 84.5percent PtO2 / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr 8: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h 9: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating 10: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene 11: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 12: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 13: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 96 percent / conc. hydrobromic acid / acetic acid / 41 h / Heating 2: 96 percent / K2CO3 / acetone; dimethylformamide / 64 h / Ambient temperature 3: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C 4: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature 5: 69 percent / hydrogen / 84.5percent PtO2 / ethanol / 2.75 h / 2327.2 Torr 6: 111 g / pyridine / 1.42 h / 5 °C 7: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride 8: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C 9: 81 percent / hydrogen / 84.5percent PtO2 / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr 10: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h 11: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating 12: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene 13: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 14: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 15: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 2: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 3: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 2: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 2: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 3: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 78 percent / aq. NaOH / methanol; dimethylformamide / 0.5 h / 40 - 50 °C 2: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 3: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 4: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

chloro-trimethyl-silane; triethylamine; sodium iodide 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min; Yield given. Multistep reaction;