Multi-step reaction with 11 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 2.5 h / Reflux
2.1: triethylamine / dichloromethane / 0 °C
3.1: sodium tetrahydroborate / nickel(II) chloride hexahydrate / methanol / 5 - 23 °C
4.1: hydrogenchloride; benzotriazol-1-ol / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C
6.1: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C
7.1: hydrogenchloride / water; methanol / 1 h / 50 °C
8.1: sodium cyanoborohydride; acetic acid / methanol / 26 h / 20 °C
9.1: chloroform / 0.33 h / 0 °C
10.1: acetonitrile / 20 h
11.1: sodium hydroxide; water / ethanol / 0.5 h / 50 °C
11.2: 0 °C
With
hydrogenchloride; ammonium hydroxide; sodium tetrahydroborate; thionyl chloride; water; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; triethylamine; N,N-dimethyl-formamide; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide;
nickel(II) chloride hexahydrate;
In
1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; chloroform; water; acetonitrile;