sodium tetrahydroborate; nickel dichloride in methanol T=0°C; 0.25 h;

sodium tetrahydroborate; nickel dichloride in methanol Ambient temperature;

1: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature 2: 80 percent / NaBH4, NiCl2*6H2O / methanol / 0.25 h / 0 °C View Scheme

1: 88 percent / NaN3, HCl / methanol; H2O / 0.5 h / -78 °C 2: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature 3: 80 percent / NaBH4, NiCl2*6H2O / methanol / 0.25 h / 0 °C View Scheme

1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature View Scheme

1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature View Scheme

1: 92 percent / formic acid / 0 °C 2: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 3: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 4: 62 percent / TBAF / tetrahydrofuran / 0 °C View Scheme