Multi-step reaction with 11 steps
1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 8 h / Reflux
2.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.5 h / 20 °C
2.2: 4 h / 20 °C
3.1: toluene / 2 h / Reflux
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 0 - 20 °C
5.1: hydrogen / Raney-Ni / ethanol; water / 4 h
6.1: dmap; triethylamine / dichloromethane / 24 h / 20 °C
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / -78 - 20 °C
7.2: 0.25 h / -78 °C
8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
9.1: calcium chloride; sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
9.2: pH 3 - 4
10.1: Chiralpak AD-H / hexane; ethanol / Resolution of racemate
11.1: hydrogenchloride / dichloromethane; diethyl ether / 0.17 h / 0 °C
With
hydrogenchloride; dmap; sodium tetrahydroborate; osmium(VIII) oxide; water; hydrogen; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; calcium chloride; lithium hexamethyldisilazane;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; toluene;
1.1: Suzuki Coupling;