Multi-step reaction with 9 steps
1: 52 percent / ethanol / 12 h / Heating
2: 1.) NaH / 1a.) toluene, 60 deg C, 30 min, 1b.) 100 deg C, 10 min, 2.) reflux
3: 67 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
4: 98 percent / N-methylmorpholine N-oxide, tris(triphenylphosphine)ruthenium(II) dichloride / acetone / 20 h / Ambient temperature
5: 1.) sodium hydride / 1.) THF, 0 deg C, 40 min, 2.) RT, 2 h
6: 1.) 1.2 M diisobutylaluminum hydride, water / 1a.) THF, toluene, 0 deg C, 1 h, 1b.) RT, 1.5 h, 2.) 1 h
8: 1.) 1 M triethylborane, 2.) sodium borohydride / 1.) THF, 20 deg C, 140 min, 2.) -75 deg C, 12 h
9: H2, triethylamine / 10percent Pd/C / methanol / 0.33 h / Ambient temperature
With
sodium tetrahydroborate; lithium aluminium tetrahydride; tris(triphenylphosphine)ruthenium(II) chloride; triethyl borane; water; hydrogen; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; acetone;
DOI:10.1021/jm00163a011