2,6-dimethylpyridine; tetraethylammonium bromide; Xtalfluor-E® in dichloromethane T=21°C; Inert atmosphere;

N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; Alkylation;

toluene-4-sulfonic acid; lithium bromide T=20°C; 16 h;

1: 69 percent / HMPA; BuLi / tetrahydrofuran; hexane / -15 - 0 °C 2: 85 percent / NBS; PPh3 / dimethylformamide / 1 h / 0 °C 3: 73 percent / BuLi / tetrahydrofuran; hexane / -78 - 20 °C 4: NBS / acetone; H2O / 0.02 h / -30 °C 5: 97 percent / LiAlH4 / diethyl ether / 20 °C 6: 92 percent / Et3N / CH2Cl2 / 2 h / 20 °C 7: 95 percent / LiAlH4 / diethyl ether / 16 h / 20 °C 8: 97 percent / D2 / RhCl(PPh3)3 / benzene / 36 h 9: 89 percent / aq. HCl / methanol / 24 h / 20 °C 10: IBX / dimethylsulfoxide / 12 h / 20 °C 11: 88 mg / H2SO4; CrO3 / acetone; H2O View Scheme