1: 65 percent / 2-hydroxypyridine; Et3N 2: TMSCl; phenol / CH2Cl2 View Scheme

1: 88 percent / OsO4; NMMO / 2-methyl-propan-2-ol; acetone; H2O 2: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 3: (COCl)2 / dimethylformamide; toluene / 1 h 4: NEt3 / CH2Cl2 5: 100 percent / H2 / Pd/C / ethyl acetate 6: (COCl)2 / toluene; dimethylformamide / 1 h 7: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 8: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 9: NEt3 / CH2Cl2 10: 85 percent / NaN3; 15-crown-6; DMPU 11: 59 percent / 2-OH-pyridine; NEt3 12: H2; aq. HCl / Pd/C / methanol View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine / anhydrous dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 6.2: 12.5 h / 0 - 5 °C 7.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 7.2: 0.5 h / 0 - 5 °C 8.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 8.2: 14.25 h / 0 - 30 °C 9.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 10.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 11.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 12.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 5.75 h / 0 - 30 °C 3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 4.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 4.2: 12.5 h / 0 - 5 °C 5.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 5.2: 0.5 h / 0 - 5 °C 6.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 6.2: 14.25 h / 0 - 30 °C 7.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 8.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 9.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 10.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 2.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 5.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 5.2: 12.5 h / 0 - 5 °C 6.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 6.2: 0.5 h / 0 - 5 °C 7.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 7.2: 14.25 h / 0 - 30 °C 8.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 9.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 10.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 11.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: iodine; magnesium; .alpha.-butylene bromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 2 h / -78 °C 1.3: -78 °C 2.1: hydrogenchloride; hydrogen; acetic acid / platinum(IV) oxide / water / 3 h / 20 °C / 760.05 Torr 3.1: sodium hydroxide; water / ethanol / 3 h / 50 °C 3.2: 20 °C 3.3: pH 1 - 2 4.1: triethylamine; 2-hydroxy-pyridine / tert-butyl methyl ether / 18 h / 80 °C 5.1: hydrogen; acetic acid / palladium 10 on activated carbon / ethanol / 20 °C / 760.05 Torr 5.2: pH 10 View Scheme

1: ammonia / methanol / 12 h / 25 - 30 °C 2: hydrogen; ammonia / raney nickel / methanol / 14 h / 40 - 45 °C / 2942.29 Torr 3: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 4: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 1 h / 0 - 5 °C 2.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 3.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 4.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 5.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: hydrogenchloride / dichloromethane; water / 10 - 30 °C / pH 1.8 1.2: 0 - 80 °C 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 2.2: 12.5 h / 0 - 5 °C 3.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 3.2: 0.5 h / 0 - 5 °C 4.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 4.2: 14.25 h / 0 - 30 °C 5.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 6.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 7.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 8.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1: H2 / Pd()OH)2/C 2: 65 percent / 2-hydroxypyridine; Et3N 3: TMSCl; phenol / CH2Cl2 View Scheme