Multi-step reaction with 11 steps
1.1: magnesium; sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1.5 h / Inert atmosphere; Reflux
1.2: 1.5 h / 50 °C / Inert atmosphere
2.1: tetrahydrofuran / 2.5 h / 20 - 45 °C / Inert atmosphere
3.1: sodium periodate / tetrahydrofuran; water / 1.5 h / 60 °C / Inert atmosphere
4.1: hydrogen; palladium(II) trifluoroacetate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine / dichloromethane / 20 °C / 3000.3 Torr
5.1: sodium tetrahydroborate / tetrahydrofuran; isopropyl alcohol / -10 - 20 °C / Inert atmosphere
6.1: thionyl chloride / tetrahydrofuran / 90 h / 10 - 15 °C / Inert atmosphere
7.1: potassium carbonate / 35 h / 90 - 95 °C / Inert atmosphere
8.1: 75 - 80 °C / Inert atmosphere
9.1: ammonium hydroxide / water; tert-butyl methyl ether / Inert atmosphere
9.2: 20 - 25 °C / Inert atmosphere
10.1: acetone / Reflux; Inert atmosphere
11.1: ammonium hydroxide; water / ethyl acetate / Inert atmosphere
11.2: Reflux; Inert atmosphere; Resolution of racemate
With
(R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; thionyl chloride; palladium(II) trifluoroacetate; water; hydrogen; potassium carbonate; magnesium; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; dichloromethane; tert-butyl methyl ether; water; ethyl acetate; isopropyl alcohol; acetone; toluene;