Multi-step reaction with 12 steps
1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol; tetrahydrofuran / 6 h / 25 °C
2: sodium periodate; water / tert-butyl alcohol; tetrahydrofuran / 8 h / 25 °C
3: toluene-4-sulfonic acid / toluene / 25 - 120 °C
4: hydrogen / palladium on carbon / ethanol / 25 °C / Inert atmosphere
5: water; lithium chloride / dimethyl sulfoxide / 16 h / 90 °C
6: cerium(III) chloride heptahydrate / 3 h / 100 °C
7: diisobutylaluminium hydride / dichloromethane / 4 h / -78 °C
8: dipyridinium dichromate / dichloromethane / 25 °C
9: tetrahydrofuran / 2 h / 0 °C
10: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 °C
11: hydrazine hydrate / ethanol / 25 °C
12: N-ethyl-N,N-diisopropylamine / butan-1-ol / 25 - 110 °C
With
sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; water; hydrogen; diisobutylaluminium hydride; hydrazine hydrate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride;
palladium on carbon; toluene-4-sulfonic acid;
In
tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; toluene; tert-butyl alcohol; butan-1-ol;