1: 1.) diisopropylethylamine, dibutylboryl triflate (n-Bu2BOTf), 2.) N-bromosuccinimide (NBS) / 1.) CH2Cl2, a.) -78 deg C, 15 min, b.) 0 deg C, 1 h, 2.) -78 deg C, 1.25 h 2: tetramethylguanidinium azide (TMGA) / CH2Cl2 / 3 h / 0 °C 3: 96 percent / lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 0 °C 4: 92 percent / H2 / 10percent Pd/C / H2O; acetic acid / 4 h / 760 Torr View Scheme

1.1: titanium tetrachloride / dichloromethane / 0 °C / |Inert atmosphere 1.2: Mannich Aminomethylation / 0 °C / |Inert atmosphere 1.3: Mannich Aminomethylation / 16 h / -80 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / |Inert atmosphere 2.2: 0 °C / |Inert atmosphere 3.1: water; mercury(II) trifluoroacetate / tetrahydrofuran / 20 °C / |Inert atmosphere 4.1: hydrogen; water; palladium 10 on activated carbon; acetic acid / methanol / 16 h / 750.08 Torr 5.1: water; sodium hydrogencarbonate / 1,4-dioxane / 8 h / 20 °C / |Inert atmosphere View Scheme

1: 78 percent / TiCl4, Et3N / CH2Cl2 / 60 h / 0 °C 2: 76 percent / H2O2, LiOH*H2O / H2O; tetrahydrofuran / 1 h / 0 °C 3: 65 percent / aq. HCl / acetic acid / 48 h / Heating View Scheme