Multi-step reaction with 9 steps
1.1: tert.-butyl lithium / tetrahydrofuran / 0.75 h / 0 °C
1.2: 3 h
2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 25 °C
3.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 90 °C
4.1: triethylamine / tetrahydrofuran / 3 h
5.1: sodium azide / N,N-dimethyl-formamide / 72 h / 110 °C
6.1: hydrazine / methanol / 12 h / 60 °C
7.1: tetrahydrofuran / 0.5 h / 25 °C
8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h
8.2: 2 h / 25 °C
9.1: triethylsilane; water; trifluoroacetic acid / dichloromethane / 0.5 h / 25 °C
With
triethylsilane; sodium azide; water; tert.-butyl lithium; sodium hydrogencarbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; hydrazine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja203198y