Multi-step reaction with 10 steps
1.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 18 h / 20 °C / Inert atmosphere
3.1: hydrogen azide; di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane; N,N-dimethyl-formamide; toluene / 2 h / -20 °C / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran / 0.12 h / 0 - 20 °C / Inert atmosphere
7.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
7.2: 0 - 20 °C / Inert atmosphere
8.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
9.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
9.2: 0 - 20 °C / Inert atmosphere
10.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 20 °C / 750.08 Torr / Inert atmosphere
With
hydrogen azide; 1-hydroxy-7-aza-benzotriazole; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; lithium hydroxide;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1002/chem.201200457