Multi-step reaction with 8 steps
1: 94 percent / NH3, AlMe3 / 1,1,2-trichloro-ethane; toluene / 60 h / Heating
2: 96 percent / Et3N / CH2Cl2 / 2 h / 0 °C
3: 92 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating
4: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min
5: Et3N / CH2Cl2 / 24 h / 0 °C
6: tetrahydrofuran / 48 h / 80 °C
7: lithium aluminium hydride / tetrahydrofuran / 8 h / Heating
8: Et3N / CH2Cl2 / 12 h / Ambient temperature
With
sodium tetrahydroborate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; borane; ammonia; dihydrogen peroxide; trimethylaluminum; triethylamine; tert-butyl alcohol;
In
tetrahydrofuran; dichloromethane; 1,1,2-trichloroethane; toluene;
DOI:10.1021/jo00383a026