1: 2,6-bis-(hydroxymethyl)-pyridine With sodium hydride in tetrahydrofuran T=20°C; 0.75 h; 2: tert-butyldimethylsilyl chloride in tetrahydrofuran T=20°C; 0.75 h;

2: 89 percent / imidazole / dimethylformamide / 0.25 h / Ambient temperature 3: 1) BuLi / 1) THF-Et2O-hexane, -78 deg C, 2) -78 deg C -> -50 deg C 4: NaBH4 / methanol / Ambient temperature View Scheme

1: 1) BuLi / 1) THF-Et2O-hexane, -78 deg C, 2) -78 deg C -> -50 deg C 2: NaBH4 / methanol / Ambient temperature View Scheme

1: 89 percent / imidazole / dimethylformamide / 0.25 h / Ambient temperature 2: 1) BuLi / 1) THF-Et2O-hexane, -78 deg C, 2) -78 deg C -> -50 deg C 3: NaBH4 / methanol / Ambient temperature View Scheme

1.1: lithium borohydride / tetrahydrofuran / 16 h / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2.2: 12 h View Scheme

1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 3 h / 20 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / |Reflux View Scheme

1: thionyl chloride; methanol / 16 h / |Reflux 2: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 20 °C 3: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 3 h / 20 °C 4: sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / |Reflux View Scheme