Multi-step reaction with 11 steps
1.1: camphor-10-sulfonic acid / toluene / 24 h / Reflux
2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.33 h / -78 °C
2.2: -78 °C
3.1: n-butyllithium / tetrahydrofuran; hexanes / 0.17 h / -78 °C
3.2: -78 - 20 °C
3.3: 4 h / Reflux; Inert atmosphere
4.1: sodium hydrogencarbonate / diphenylether / 4 h / 180 °C
5.1: camphor-10-sulfonic acid / 5 h / Reflux
6.1: hydrogenchloride; water / acetone / 20 °C
7.1: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 24 h / 20 °C
8.1: dichloromethane / 20 °C
9.1: ammonium chloride; zinc / methanol; water / 24 h / Reflux
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
11.1: trifluoroacetic acid / dichloromethane / 20 °C
With
hydrogenchloride; n-butyllithium; water; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc;
camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; hexanes; diphenylether; dichloromethane; water; acetone; toluene;