Multi-step reaction with 11 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C
1.2: 0 - 20 °C
2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C
3.1: methanol; sodium hydroxide; water / 20 °C
3.2: pH 7
4.1: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
5.1: methanol; water
6.1: methanol; water; sodium carbonate / 14 h / 20 °C
7.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C
7.2: 48 h / 0 - 20 °C
8.1: methanol; water; sodium carbonate / 14 h / 20 °C
9.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C
9.2: 22 h / 0 - 20 °C
10.1: hydrogen / palladium(II) hydroxide/carbon / ethanol / 36 h / 60 °C
11.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16.5 h / 20 °C / Molecular sieves 3 ?
With
methanol; dmap; sodium hydroxide; di-isopropyl azodicarboxylate; water; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; sodium carbonate; triethylamine; triphenylphosphine;
palladium(II) hydroxide/carbon;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;