1: 1,1-dimethylethyl[6-chloro-2-pyridinyl]carbamate With n-butyllithium; N,N,N',N'-tetraethyl ethylenediamine in tetrahydrofuran; hexane T=-78 - -10°C; 2 h; Inert atmosphere; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78 - 20°C; 1 h; 3: With hydrogenchloride; water in tetrahydrofuran; hexane T=-10°C; pH=2 - 3;

1.1: 85 percent / NaHMDS / tetrahydrofuran / 0.25 h / 20 °C 2.1: BuLi; TMEDA / tetrahydrofuran; hexane / 2 h / -78 - -10 °C 2.2: 65 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: 85 percent / NaHMDS / tetrahydrofuran / 0.25 h / 20 °C 2.1: BuLi; TMEDA / tetrahydrofuran; hexane / 2 h / -78 - -10 °C 2.2: 65 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: tetrahydrofuran / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: N,N,N',N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran / -78 - -10 °C / Inert atmosphere 2.2: 20 °C View Scheme

1: methanol / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere View Scheme

1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 4 h / 20 °C 2: hydrogenchloride / 1,4-dioxane / 0.5 h 3: trifluoroacetic anhydride; pyridine / 1,4-dioxane / 0 - 60 °C View Scheme