Multi-step reaction with 10 steps
1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 3 h / -70 °C
2.1: triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane / dichloromethane / 2.75 h / -78 - -65 °C / Inert atmosphere
2.2: 3.25 h / -78 - -67 °C
3.1: water; dihydrogen peroxide; sodium hydroxide / methanol; tert-butyl alcohol / 0 - 20 °C
3.2: pH 4
4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 65 °C / Inert atmosphere
7.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 14 h / 0 °C
9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 3 h / -78 - 20 °C
10.1: solid-phase supported CuPF6 / toluene / 16 h / 55 °C
With
2,6-dimethylpyridine; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; dihydrogen peroxide; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/ja105119r