Multi-step reaction with 9 steps
1: Et3N / CH2Cl2 / 5 h / -30 - 20 °C
2: 0.191 g / NaN3 / dimethylformamide / 15 h / 70 °C
3: PPh3; H2O / tetrahydrofuran / 24 h / 20 °C
4: 0.135 g / tetrahydrofuran / 24 h / 20 °C
5: 100 percent / H2 / Pd/C / ethyl acetate / 3 h / 20 °C
6: 0.135 g / 2,4,6-trimethylpyridine; 7-aza-1-hydroxybenzotriazole / ethyl acetate / 15 h / 20 °C
7: aq. HCl / ethyl acetate / 3 h / 20 °C
8: 0.122 g / 2,4,6-trimethylpyridine; i-Pr2NEt / acetonitrile / 16 h / 20 °C
9: Et2NH / acetonitrile / 0.67 h / 20 °C
With
2,4,6-trimethyl-pyridine; hydrogenchloride; sodium azide; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.200400977