sodium tetrahydroborate in methanol T=20°C; 2 h; Inert atmosphere;

1: 68 percent / NaBH4 / methanol / 1.) 1 h, room temp., 2.) 0.5 h, reflux 2: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating 3: 92 percent / H2 / PtO2 / acetic acid 4: 92 percent / Na / liquid ammonia / 0.5 h View Scheme