hydrogen; nickel in ethanol T=20°C; 29 h;

1: 1.) NaH / 1.) DMF, room temp., 3 h; 2.) pH=8, room temp., 30 min 2: 93 percent / hydrogen / Raney-Ni / ethanol / 29 h / 20 °C View Scheme

1: 1.) cc. HCl; 2.) aq. K2CO3 / 1.) AcOH, 2 deg C, 15 min; 2.) pH=6, 5 deg C, 2 h 2: 1.) aq. NaOH; 2.) aq. HCl / 1.) MeOH, room temp., 90 min; 2.) 0 deg C, 3 h, pH=2 3: 96 percent / cc. HBr / 22 h / 100 °C 4: 84 percent / HCl / 4 h / 0 °C 5: 85 percent / NaBH4 / methanol; tetrahydrofuran / 2 h / 25 °C View Scheme