Multi-step reaction with 15 steps
1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h
1.2: 12 h / 20 °C
2.1: palladium dichloride; triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 15 h / 110 °C / Schlenk technique; Inert atmosphere
3.1: magnesium; methanol / 13 h / Reflux
4.1: Amano lipase PS-IM (immobilized on diatomaceous earth) / water; di-isopropyl ether / 65 h / 40 °C / Resolution of racemate; Enzymatic reaction
5.1: copper(I) bromide dimethylsulfide complex; methanol / diethyl ether / 5 h / 0 - 20 °C / Reflux
6.1: pyridine; dmap / dichloromethane / 13 h / 20 °C
7.1: dimethyl sulfoxide / 10 h / 60 °C
8.1: ethylene glycol; potassium hydroxide / water / 12 h / 110 °C
9.1: trifluoroacetic acid; trifluoroacetic anhydride / 0.08 h / 0 °C
10.1: aluminum (III) chloride; methoxybenzene / 3 h / 100 °C
11.1: dmap / dichloromethane / 3 h / Schlenk technique
12.1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 20 °C / Schlenk technique
13.1: phosphoric acid / N,N-dimethyl-formamide / 4.5 h / 80 - 100 °C / Schlenk technique
14.1: thallium(III) nitrate trihydrate / acetonitrile / 0.08 h / -40 °C / Schlenk technique; Inert atmosphere
14.2: 0.33 h / -20 °C
15.1: pyridine; triethylamine / dichloromethane / 21 h / 20 °C
With
pyridine; methanol; dmap; aluminum (III) chloride; sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; thallium(III) nitrate trihydrate; phosphoric acid; Amano lipase PS-IM (immobilized on diatomaceous earth); magnesium; ethylene glycol; methoxybenzene; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; trifluoroacetic anhydride; potassium hydroxide; palladium dichloride;
In
methanol; diethyl ether; dichloromethane; di-isopropyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.201202413