1: 1.) ethylene glycol, p-toluenesulphonic acid 2.) KOH / 1.) ethylene glycol, p-toluenesulphonic acid 2.) KOH, ethanol/water (2:1) 2: 18 percent / DCC 3: 65 percent / 30 h / Irradiation 4: 98 percent / HCl / methanol View Scheme

diethylamino-sulfur trifluoride T=20°C; Neat (no solvent);

potassium hydroxide; triethanolamine; hydrazine hydrate T=195°C;

1.1: toluene / 16 h / Reflux; Inert atmosphere 2.1: sulfuric acid / 2.5 h / 90 - 92 °C / Inert atmosphere 2.2: 5 - 18 °C / pH 7 / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.27 h / 5 °C / Inert atmosphere 3.2: 0.5 h / 5 - 20 °C / Inert atmosphere View Scheme

1: alkali; alcohol / Hydrolysis 2: Erhitzen ueber den Schmelzpunkt View Scheme

1: SF4 / CH2Cl2; H2O 2: (i) NaOEt, EtOH, (ii) aq. KOH View Scheme

pyridinium p-toluenesulfonate in toluene 2 h; Reflux;

1.1: toluene / 16 h / Reflux; Inert atmosphere 2.1: sulfuric acid / 2.5 h / 90 - 92 °C / Inert atmosphere 2.2: 5 - 18 °C / pH 7 / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 2.33 h / 65 - 67 °C / Inert atmosphere 3.2: 3 h / 10 - 20 °C / Inert atmosphere 4.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium / N,N-dimethyl-formamide / 7 h / 85 °C / Inert atmosphere 5.1: CDX-017 enzyme; pyridoxal 5'-phosphate / water; dimethyl sulfoxide / 52 h / 45 °C / pH 8.5 / Inert atmosphere; triethanolamine/isopropylamine buffer; Enzymatic reaction 5.2: 2 h / pH 6 / Inert atmosphere 6.1: sodium carbonate / isopropanol acetate; water / 0.08 h / 20 °C / Inert atmosphere 6.2: 2 h / 20 °C / Inert atmosphere 7.1: potassium carbonate / N,N-dimethyl-formamide / 2.08 h / Inert atmosphere 8.1: lithium hydroxide hydrate / tetrahydrofuran; water / 4.25 h / 15 - 20 °C / Inert atmosphere 8.2: 2 h / pH 2.5 - 3.5 / Inert atmosphere View Scheme

1: Br2 / diethyl ether 2: ethanol 3: 95 percent / Na, Et2O 4: 86 percent / HCl / Heating View Scheme

1: Br2 / diethyl ether 2: ethanol 3: 95 percent / Na, Et2O 4: 86 percent / HCl / Heating 5: 67 percent / NH3, H2 / Raney Ni / ethanol / 22 h / 90 °C / 67505.4 Torr View Scheme