1: NaBH4 / methanol / 1 h / -30 °C 2: Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 4 h / Ambient temperature 3: 92 percent / p-TsOH / CH2Cl2 / 12 h / Ambient temperature 4: 39 percent / n-Bu3SnH, azobis(isobutyronitrile) (AIBN) / benzene / 1 h / Heating 5: 1.) p-toluenesulfinic acid, 2.) Et3N, 4-(N,N-dimethylamino)pyridine / 1.) CH3CN, H2O, RT, 48 h, 2.) CH2Cl2, 3 h 6: 1.) ozone, oxygen, 2.) dimethyl sulfide / 1.) CH2Cl2, 2.) 10 h 7: NaBH4 / methanol / 1 h / -40 °C 8: 93 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 27 h 9: 50percent methanolic ammonia / 4 h 10: 67 percent / pyridine / 27 h 12: 97 percent / Lawesson's reagent / toluene / 1 h / Heating 13: 96 percent / W-2 Raney Ni / ethanol / 1 h / Heating 14: 63 percent / aq. MeNH2 / methanol / 46 h View Scheme