Multi-step reaction with 10 steps
1.1: dmap; triethylamine / dichloromethane / 20 °C
2.1: nitric acid / nitromethane / 1 h / 0 °C
3.1: manganese(IV) oxide / dichloromethane / 24 h / Molecular sieve; Reflux
4.1: tin(II) chloride dihdyrate / ethanol / 2 h / Reflux
5.1: tetrahydrofuran / 16 h / 20 °C
6.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
6.2: -78 - 20 °C / Inert atmosphere
7.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / tetrahydrofuran / 0.08 h
7.2: 1 h
8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
9.1: potassium carbonate / methanol; water / 20 h / 65 °C
10.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran; 1,2-dichloro-ethane / Molecular sieve
With
dmap; manganese(IV) oxide; tin(II) chloride dihdyrate; tert.-butyl lithium; nitric acid; sodium tris(acetoxy)borohydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; nitromethane; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2011.09.001