1: Boc2O; DMAP 2: NaOH / methanol; H2O View Scheme

1: 1.) N-hydroxysuccinimide, DCC; 2.) NaBH4 / 1.) CH2Cl2, r.t., 3 h; 2.) THF, EtOH, 0 deg C, 15 min 2: p-TsOH / CH2Cl2 / Ambient temperature 3: LiAlH4 / diethyl ether / 0.33 h / 0 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / |Inert atmosphere 2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 20 °C / |Inert atmosphere 3: diisobutylaluminium hydride / diethyl ether / 1 h / -78 °C / |Inert atmosphere 4: sodium tetrahydroborate / tetrahydrofuran; water / 0.5 h / 0 °C / |Inert atmosphere 5: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 6: cerium(III) chloride heptahydrate; sodium iodide / acetonitrile / 20 °C / |Inert atmosphere 7: neat (no solvent) / 2 h / 80 °C / |Inert atmosphere 8: tris-(dibenzylideneacetone)dipalladium(0); diethylamine; 1,2-bis-(diphenylphosphino)ethane / tetrahydrofuran / 20 °C / |Inert atmosphere 9: potassium phosphate / chlorobenzene / 15 h / 90 °C / |Inert atmosphere 10: |Inert atmosphere View Scheme