Multi-step reaction with 7 steps
1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -50 °C
2: NMO, 3 Angstroem molecular sieves, TPAP / acetonitrile / 0.5 h / 25 °C
3: 89 percent / 2-methylbut-2-ene, NaClO2, H2O, Na2HPO4 / tetrahydrofuran; 2-methyl-propan-2-ol / 8 h / 25 °C
4: 82 percent / DCC, DMAP / CH2Cl2 / 2 h / Ambient temperature
5: 82 percent / KHMDS / tetrahydrofuran; toluene / 1.) -78 deg C, 30 min, 2.) r.t., 30 min
6: LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) reflux, 2 h
7: ammonium formate / 10 percent Pd/C / methanol / 0.5 h / Heating
With
dmap; sodium chlorite; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 3 A molecular sieve; water; ammonium formate; potassium hexamethylsilazane; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1039/a809925a