Multi-step reaction with 12 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C
1.2: 1 h / -78 °C
2.1: hydrogen; quinoline / ethyl acetate / 0.67 h
3.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere
3.2: 0.17 h / -20 °C / Inert atmosphere
3.3: 24 h / -20 - 0 °C / Inert atmosphere
4.1: hydrogen; 20% palladium hydroxide-activated charcoal / ethyl acetate; ethanol / 0.5 h / 3345.86 Torr
5.1: sodium periodate / dichloromethane; water / 0.5 h / 0 °C / Cooling with ice
6.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
7.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
7.2: 20 °C
8.1: triethylamine / ethyl acetate / 5 h / 20 °C / Reflux
9.1: dipotassium hydrogenphosphate; sodium carbonate; codexis BS3 / water; dimethyl sulfoxide; methanol / 7 h / 0 - 25 °C / pH 7 - 8 / Enzymatic reaction
9.2: 0.5 h / 5 - 40 °C / pH Ca. 10
10.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
11.1: acetic acid / methanol; tetrahydrofuran / 0.17 h / 20 °C
11.2: MP-CN BH3 / 20 °C
12.1: trifluoroacetic acid / dichloromethane / 20 °C
12.2: 0 °C / pH Ca. 5
With
quinoline; hydrogenchloride; sodium tetrahydroborate; sodium periodate; dipotassium hydrogenphosphate; n-butyllithium; 20% palladium hydroxide-activated charcoal; codexis BS3; hydrogen; diethylzinc; sodium carbonate; Dess-Martin periodane; acetic acid; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;