Multi-step reaction with 10 steps
1: 1.) NaH; 2.) DIBAL / 1.) THF, 0 deg C; 2.) toluene, 0 deg C
2: 34 percent / diethyl azodicarboxylate, triphenylphosphine
3: 75 percent / N,N-dimethylaniline / 0.83 h / Heating
4: 83 percent / K2CO3 / dimethylformamide / 9 h / 80 °C
5: 1.) O3; 2.) sodium borohydride / 1.) MeOH, CH2Cl2, -78 deg C, 12 min; 2.) -78 deg C to r.t.
6: 86 percent / diethyl azodicarboxylate, triphenylphosphine
7: 96 percent / hydrazine hydrate / ethanol / 2.5 h / Heating
8: 90 percent / 0.75 h / 0 deg C to r.t.
9: 89 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating
10: 85 percent / 1 h / 0 deg C to r.t.
With
sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; hydrazine hydrate; N,N-dimethyl-aniline; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.1246/cl.1985.505