Multi-step reaction with 12 steps
1.1: 0.17 h / 210 °C
2.1: trichlorophosphate / N,N-dimethyl-formamide / 12 h / 80 °C
3.1: acetyl chloride; sodium iodide / acetonitrile / 3 h / 50 °C
4.1: (1R,2S)-1-Amino-2-indanol; borane Ν,Ν-diethylaniline complex / tetrahydrofuran / 28 h / 0 - 20 °C
5.1: 2,6-dimethylpyridine / tetrahydrofuran / 12 h / 0 - 20 °C
6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; tetrahydrofuran / 12 h / 85 °C / Inert atmosphere; Reflux
7.1: diisobutylaluminium hydride / dichloromethane / 2 h / 0 °C
7.2: 0.08 h
8.1: Dess-Martin periodane / dichloromethane / 12 h / 0 - 20 °C
9.1: isopropylmagnesium chloride / tetrahydrofuran / 5 h / -20 °C
9.2: 12 h / -40 - 20 °C
9.3: 0.5 h / 0 °C
10.1: cesium fluoride / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 36 h / 50 °C / Inert atmosphere
11.1: Iodine monochloride / dichloromethane / 24 h
12.1: triethylamine; hydrogen / palladium on activated charcoal / methanol / 12 h / 7500.75 Torr
With
2,6-dimethylpyridine; borane Ν,Ν-diethylaniline complex; (1R,2S)-1-Amino-2-indanol; hydrogen; isopropylmagnesium chloride; Iodine monochloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; acetyl chloride; cesium fluoride; sodium iodide; trichlorophosphate;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;