1: NaBH4 / methanol / 3 h / Heating 2: NaIO4 / 0.5 h / Ambient temperature 3: 2.42 g 4: 73 percent / p-(dimethylamino)pyridine, triethylamine / tetrahydrofuran / 16 h / Ambient temperature 5: 44.7 percent / silver trifluoroacetate / CH2Cl2 / 2 h / Ambient temperature 6: 87 percent / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 7: 108 mg / 0.13M NaOH / acetone / 2 h 8: 1.) triethylamine, ethyl chloroformate, 2.) sodium azide 9: 98.6 percent / O3 / CH2Cl2 / 0.25 h / -78 °C 10: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 11: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 12: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 13: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme

1: NaBH4 / methanol / 3 h / Heating 2: NaIO4 / 0.5 h / Ambient temperature 3: NaBH4 / 1 h / Ambient temperature 4: 968 mg / acetic anhydride, pyridine / Ambient temperature 5: 1.) NH3, 2.) pyridine / 1.) methanol, room temperature 6: 1.) Pb(OAc)4, 2.) triethylamine 7: 97 percent / 2M HCl / methanol / 1 h / Heating View Scheme