Multi-step reaction with 8 steps
1: 93 percent / NaBH4 / methanol / 1 h / 0 °C
2: 1.) BuLi, 2.) BuLi, copper(I) iodide / 1.) THF, hexane, 0 deg C to RT, 6 h, 2.) THF, hexane, 0 deg C to RT, 16 h
3: 77 percent / KOH / tetrabutylammonium hydrogen sulfate / tetrahydrofuran / 84 h / Ambient temperature
4: 79 percent / NH3 liq. / 312 h
5: acetonitrile; H2O / 0.08 h / Ambient temperature
6: NaBH3CN, AcOH / acetonitrile; H2O / 1 h
7: 1.) potassium bis(trimethylsilyl)amide, 3.) NaH / 1.) THF, toluene, 0 deg C, 30 min, 2.) THF, toluene, 20 deg C, 24 h, 3.)THF, toluene, 20 deg C, 17 d
8: 91 percent / H2, conc. aq. HCl / Pt / methanol / 3 h / 1 Torr / Ambient temperature
With
hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; ammonia; hydrogen; potassium hexamethylsilazane; sodium hydride; sodium cyanoborohydride; acetic acid;
tetra(n-butyl)ammonium hydrogensulfate; platinum;
In
tetrahydrofuran; methanol; water; acetonitrile;