1: palladium; hydrogen / ethyl acetate / 24 h / 20 °C 2: potassium hydroxide / 1,4-dioxane; water / 36 h View Scheme

hydrogenchloride; sodium hydroxide 1.) H2O, reflux, 1 h, 2.) H2O, 3.) dioxane, 12 h; Yield given. Multistep reaction;

sodium hydroxide 1.) H2O, reflux, 24 h; 2.) H2O, dioxane, RT, 12 h; Yield givenMultistep reaction;

hydrogenchloride; lithium borohydride; triethylamine in tetrahydrofuran; methanol

hydrogenchloride; triethylamine in tetrahydrofuran; methanol

hydrogenchloride; triethylamine in tetrahydrofuran; methanol

1: Et3N / tetrahydrofuran / 0.67 h / 0 °C 2: LiBH4 / tetrahydrofuran / 6 h / 0 - 20 °C View Scheme

1: Et3N / tetrahydrofuran / 0.67 h / 0 °C 2: LiBH4 / tetrahydrofuran / 6 h / 0 - 20 °C 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT 4: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min 5: aq. LiOH / dioxane / 16 h / Ambient temperature 6: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 7: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme