Multi-step reaction with 12 steps
1.1: lithium borohydride; methanol / toluene; tetrahydrofuran / 22 h / -5 - 22 °C
2.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C
3.1: zinc / methanesulfonic acid / tetrahydrofuran / 12 h / Reflux
4.1: water; acetic acid / tetrahydrofuran / 2 h / 20 °C
5.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
6.1: toluene / 0.5 h / 100 °C
7.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 1 h / -23 - -18 °C
8.1: hydrogen fluoride / acetonitrile; water / 20 h / 20 °C
9.1: pyridine / dichloromethane / 1 h / -10 - 0 °C
10.1: sodium iodide / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 22 °C
11.1: triethylamine; nickel dichloride; chromium dichloride; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide / tetrahydrofuran / 20.5 h / 22 - 24 °C / Inert atmosphere
11.2: 1 h / 0 - 5 °C
12.1: Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C
12.2: 1 h
With
pyridine; chromium dichloride; methanol; dmap; lithium borohydride; hydrogen fluoride; water; potassium hexamethylsilazane; Dess-Martin periodane; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide; nickel dichloride; zinc; (S)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methane sulfonamide;
methanesulfonic acid;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
11.1: Nozaki-Hiyama-Kishi Coupling;