Multi-step reaction with 11 steps
1.1: 13.6 percent / sulfuric acid/silica gel; water / dioxane / 0.17 h
2.1: 81.7 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0 - 20 °C
3.1: ammonium formate / Pd/C / methanol; ethyl acetate / 2 h / Heating
4.1: 6.940 g / sodium hydrogencarbonate / acetone; H2O / 0.33 h / 0 °C
5.1: p-toluenesulfonic anhydride; triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 5 h
5.2: 92.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 24 h
6.1: thiocresol / 2 h / 110 °C
6.2: tributyltin hydride; 2,2'-diazobisisobutyronitrile / toluene / 24 h / Heating
6.3: H2; triethylamine / Pd(OH)2/C / ethyl acetate / 1 h
7.1: 1.231 g / triethylamine; potassium carbonate / acetone / 15 h
8.1: tert-butyl hypochlorite; triethylamine / CH2Cl2 / 0.33 h / 0 °C
9.1: tetrafluoroboric acid-dimethyl ether copmlex; silver tetrafluoroborate / acetone / 1 h / -10 °C
10.1: 4.2 percent / KBH4 / acetic acid / 0.5 h / 0 °C
11.1: 0.045 g / aq. hydrochloric acid / methanol
With
hydrogenchloride; dmap; silver tetrafluoroborate; potassium borohydride; tert-butylhypochlorite; sulfuric acid; p-toluenesulfonylanhydride; water; ammonium formate; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; para-thiocresol; tetrafluoroboric acid dimethyl ether complex;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; acetone;
DOI:10.1021/jo000250y