Multi-step reaction with 17 steps
1: 95 percent / sodium borohydride / methanol / 1 h / 25 °C
2: 67 percent / benzene; dioxane / 24 h / Heating
3: chlorotrimethylsilane / 25 °C
4: 72 percent / NaH, MeOH / toluene / 16 h / Heating
5: 99 percent / HOAc, H2SO4 / H2O / 72 h / Heating
6: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature
7: 60 percent / K2CO3 / ethanol; toluene / 12 h / Ambient temperature
8: 82 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature
9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to -30 deg C
10: 91 percent / lithium tetrafluoroborate / tetrahydrofuran; acetonitrile / 72 h / Heating
11: 14 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating
12: 1.) diisoamylborane, 2.) 10percent aq. NaOH, 30percent H2O2 / 1.) DMF, RT, 4 h, 2.) RT, 1 h
13: 91.9 percent / diisobutylaluminum hydride / benzene; toluene / 1 h / Ambient temperature
14: 91 percent / Na, NH3 (liquid) / tetrahydrofuran / 1.5 h / -78 °C
15: 43 percent / tetrahydrofuran / 16 h / Ambient temperature
16: 76 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating
17: 40 percent / diethyl azodicarboxylate, triphenylphosphine, imidazole, sodium hydride / tetrahydrofuran / 3 h / Heating
With
pyrrolidine; 1H-imidazole; methanol; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; lithium tetrafluoroborate; n-butyllithium; chloro-trimethyl-silane; formic acid; diisoamyl borane; sulfuric acid; ammonia; dihydrogen peroxide; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1021/ja00169a033
