lithium hydroxide in tetrahydrofuran T=0°C; Hydrolysis; 2 h;

1.1: 91 percent / aq. LiOH / tetrahydrofuran / 2 h / 0 °C 2.1: 71 percent / dicyclohexylcarbodiimide; dimethylaminopyridine / CH2Cl2 / 12 h / 0 - 22 °C 3.1: 89 percent / MCPBA / CH2Cl2 / 4 h / 0 °C 4.1: 99 percent / AgClO4 / Cp2ZrCl2 / CH2Cl2 / 1 h / 22 °C 5.1: 82 percent / LiBH4; MeOH / diethyl ether / 0.25 h / Heating 6.1: 2-nitrophenyl selenocyanate; tri-n-butylphosphine / tetrahydrofuran / 0.25 h / 0 °C 6.2: 71 percent / aq. H2O2 / tetrahydrofuran / 6 h / 22 °C 7.1: 82 percent / HCl / 3 h / 0 - 22 °C View Scheme

sodium tetrahydroborate in tetrahydrofuran; methanol T=45 - 55°C;

lithium hydroxide; water in tetrahydrofuran 2 h;

1: 11.9 g / NaBH4 / tetrahydrofuran; methanol / 45 - 55 °C 2: 16.9 g / Et3N / ethyl acetate / 1 h / -20 - -5 °C View Scheme

1: 11.9 g / NaBH4 / tetrahydrofuran; methanol / 45 - 55 °C 2: 16.9 g / Et3N / ethyl acetate / 1 h / -20 - -5 °C 3: 2.60 g / 3 h / 40 °C 4: 92 percent / AcOH / 10percent Pd/C / H2O / 1.5 h / 100 °C View Scheme