Multi-step reaction with 10 steps
1.1: sodium carbonate / dichloromethane; water
1.2: 2 h / Reflux
2.1: sodium hydroxide / water; methanol; acetone / 3.33 h / 2 °C / Cooling with ice
3.1: hydrogenchloride / water / 1 h / 0 °C / pH < 3
4.1: dmap / dichloromethane; tert-butyl alcohol / 1 h / Inert atmosphere; Reflux
5.1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; toluene / 0 - 20 °C / Inert atmosphere
6.1: sodium cyanoborohydride / acetic acid / 16 h / 0 - 20 °C
7.1: 1H-imidazole; triethylamine; thionyl chloride / dichloromethane / 2.5 h / -10 - 20 °C / Inert atmosphere
8.1: rhodium(III) chloride hydrate; sodium periodate / water; acetonitrile / 4.25 h / 0 - 20 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 20 °C / Inert atmosphere
10.1: sodium dihydrogenphosphate / water; acetonitrile; ethyl acetate / 2 h / 50 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; dmap; sodium periodate; sodium dihydrogenphosphate; thionyl chloride; rhodium(III) chloride hydrate; tetrabutylammomium bromide; sodium cyanoborohydride; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium hydroxide; sodium hydroxide;
In
methanol; dichloromethane; water; acetic acid; ethyl acetate; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.tet.2014.05.004