1: 74.2 percent / triethylamine, pyridine / 1 h / 0 °C 2: 74 percent / toluene / Heating 3: 91 percent / lithium borohydride / tetrahydrofuran / 0 - 25 °C 4: 86 percent / pyridine / 2 h / 10 °C 5: 90 percent / toluene / 9 h / Heating 6: 89 percent / HBr / acetic acid / 12 h / 70 °C View Scheme

1: triethylamine / CH2Cl2 / 6 h / Heating 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 3: ethanol; H2O / 24 h / 55 - 60 °C 4: 64 percent / 6 N aq. HCl / 24 h / 130 °C 5: 76 percent / H2 / 20percent Pd(OH)2-C / aq. acetic acid / 10 h / 2280 Torr / Ambient temperature View Scheme

1: triethylamine / CH2Cl2 / 6 h / Heating 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT 3: ethanol; H2O / 24 h / 55 - 60 °C 4: 64 percent / 6 N aq. HCl / 24 h / 130 °C View Scheme

1: 87 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 3: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 4: 45 percent / LiBH4 / tetrahydrofuran 5: 69 percent / pyridine 6: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 87 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 3: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 4: 45 percent / LiBH4 / tetrahydrofuran View Scheme