Multi-step reaction with 12 steps
1: 24 h / Inert atmosphere; Reflux
2: ammonium formate; 20% palladium hydroxide-activated charcoal / methanol; ethyl acetate / 3 h / Inert atmosphere; Reflux
3: triethylamine / dichloromethane / 23 °C / Inert atmosphere
4: trichlorophosphate / 6 h / Inert atmosphere; Reflux
5: hydrogen bromide / 72 h / Inert atmosphere; Reflux
6: tert-butyl alcohol / 48 h / 23 °C / Inert atmosphere
7: potassium carbonate / toluene; acetone / 8 h / Inert atmosphere; Reflux
8: tetrahydrofuran / 120 h / Inert atmosphere; Reflux
9: sodium cyanoborohydride / methanol / 3 h / 23 °C / Inert atmosphere
10: trifluoroacetic acid; ascorbic acid / water / 0.25 h / 20 °C / Inert atmosphere
11: sodium L-ascorbate; copper(ll) sulfate pentahydrate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; acetonitrile; water / 0.17 h / 20 °C / Inert atmosphere; Cooling with ice
12: copper(ll) sulfate pentahydrate / water; dimethyl sulfoxide / Inert atmosphere
With
copper(ll) sulfate pentahydrate; 20% palladium hydroxide-activated charcoal; hydrogen bromide; ammonium formate; sodium cyanoborohydride; potassium carbonate; sodium L-ascorbate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; ascorbic acid; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1039/c3ob42379d