1: 94 percent / hydrogen chloride; molecular sieves 3 Angstroem / 3 h / Heating 2: 87 percent / sulfur; 2,2,6,6-tetramethylpiperidine / xylene / 5 h / Heating View Scheme

hydrogenchloride; water 0.5 h; Heating;

1: 81 percent / HCl / Ambient temperature 2: 91 percent / conc aq. NH4OH / Ambient temperature 3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating 4: 77 percent / POCl3 / toluene / Heating 5: 94 percent / Br2 / tetrahydrofuran / 1 h 6: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 7: 50 percent / 70percent HClO4 / tetrahydrofuran; H2O / 3 h / Ambient temperature 8: 62 percent / borane-trimethylamine / acetic acid; tetrahydrofuran / 1 h / 0 °C 9: 1.) 5.25percent NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

1: 81 percent / HCl / Ambient temperature 2: 91 percent / conc aq. NH4OH / Ambient temperature 3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating 4: 77 percent / POCl3 / toluene / Heating 5: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 6: 74 percent / 17.5percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature 7: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 8: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

1: 81 percent / HCl / Ambient temperature 2: 91 percent / conc aq. NH4OH / Ambient temperature 3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating 4: 77 percent / POCl3 / toluene / Heating View Scheme

thionyl chloride 4.5 h;

Multi-step reaction with 5 steps 1: 81 percent / HCl / Ambient temperature2: 91 percent / conc aq. NH4OH / Ambient temperature3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating4: 77 percent / POCl3 / toluene / Heating5: 94 percent / Br2 / tetrahydrofuran / 1 h  

Multi-step reaction with 5 steps 1: 81 percent / HCl / Ambient temperature2: 91 percent / conc aq. NH4OH / Ambient temperature3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating4: 77 percent / POCl3 / toluene / Heating5: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h  

Multi-step reaction with 6 steps 1: 81 percent / HCl / Ambient temperature2: 91 percent / conc aq. NH4OH / Ambient temperature3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating4: 77 percent / POCl3 / toluene / Heating5: 94 percent / Br2 / tetrahydrofuran / 1 h6: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h  

Multi-step reaction with 7 steps 1: 81 percent / HCl / Ambient temperature2: 91 percent / conc aq. NH4OH / Ambient temperature3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating4: 77 percent / POCl3 / toluene / Heating5: 94 percent / Br2 / tetrahydrofuran / 1 h6: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h7: 50 percent / 70percent HClO4 / tetrahydrofuran; H2O / 3 h / Ambient temperature