1: 2,4,6-trimethyl-pyridine 2: 600 °C 3: LiAlH4 View Scheme

1: 94 percent / p-TsOH / benzene / 13 h / Heating 2: 98 percent / imidazole / dimethylformamide / Ambient temperature 3: 1.) LDA, potassium 1,1-dimethylpropoxide, 2.) B(OMe)3, 3.) 30percent aq. H2O2 4: 1.) (PhO)3PCH3I, 2.) Bu4NF / 1.) DMF, RT, 24 h, 2.) THF, RT, 4 h 5: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 6: 95 percent / NaBH4, MeOH / 2 h / 0 - 5 °C View Scheme

1: 98 percent / imidazole / dimethylformamide / Ambient temperature 2: 1.) LDA, potassium 1,1-dimethylpropoxide, 2.) B(OMe)3, 3.) 30percent aq. H2O2 3: 1.) (PhO)3PCH3I, 2.) Bu4NF / 1.) DMF, RT, 24 h, 2.) THF, RT, 4 h 4: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 5: 95 percent / NaBH4, MeOH / 2 h / 0 - 5 °C View Scheme

1: 1.) LDA, potassium 1,1-dimethylpropoxide, 2.) B(OMe)3, 3.) 30percent aq. H2O2 2: 1.) (PhO)3PCH3I, 2.) Bu4NF / 1.) DMF, RT, 24 h, 2.) THF, RT, 4 h 3: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 4: 95 percent / NaBH4, MeOH / 2 h / 0 - 5 °C View Scheme

1: 1.) (PhO)3PCH3I, 2.) Bu4NF / 1.) DMF, RT, 24 h, 2.) THF, RT, 4 h 2: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 3: 95 percent / NaBH4, MeOH / 2 h / 0 - 5 °C View Scheme

1: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 2: 95 percent / NaBH4, MeOH / 2 h / 0 - 5 °C View Scheme

1: 92 percent / (PhO)3PCH3I, DMAP / dimethylformamide / 20 h / Ambient temperature 2: 93 percent / p-TsOH*H2O / methanol / 2 h / Ambient temperature View Scheme

1: 95 percent / Bu4NF / tetrahydrofuran / 4.5 h / Ambient temperature 2: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 3: 95 percent / NaBH4, MeOH / 2 h / 0 - 5 °C View Scheme

1: 100 percent / ethanolic KOH 2: 70 percent / MeLi / dimethylformamide / 18.5 h / Ambient temperature View Scheme