Multi-step reaction with 8 steps
1: 93 percent / Et3N / dioxane; H2O / 30 °C
2: HCl / 1) r.t., 24h, 2) 40 deg C, 24h
3: 91 percent / p-toluenesulfonic acid / 1) r.t., 2h, 2) 38 deg C., 1h
4: 99.7 percent / NaBH4 / ethanol
5: pyridine / Ambient temperature
6: 99 percent / t-BuOK, DMSO / benzene / 0.17 h / Ambient temperature
7: 94 percent / osmium tetroxide / dioxane / 0.25 h / Ambient temperature
8: 1) LiCl, DBU / 1) THF, r.t., 10 min, 2) THF, r.t., overnight
With
pyridine; hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; potassium tert-butylate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride;
In
1,4-dioxane; ethanol; water; benzene;
DOI:10.1246/bcsj.63.2224