Multi-step reaction with 9 steps
1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 15 h / 3 - 20 °C / Inert atmosphere
2.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 65 °C / Inert atmosphere
2.2: 12 h / Reflux
3.1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: cesium fluoride / N,N-dimethyl-formamide / 5 h / 85 °C
5.1: hydrogen / palladium on activated charcoal / ethanol / 1.5 h / 40 °C
6.1: 2,6-dimethylpyridine / dichloromethane / 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 - 20 °C / pH 7
8.1: trifluoroacetic acid / dichloromethane / 20 °C
9.1: sodium tris(acetoxy)borohydride / acetic acid / N,N-dimethyl-formamide / 20 °C
With
2,6-dimethylpyridine; dimethylsulfide borane complex; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium tris(acetoxy)borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal; acetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;