Multi-step reaction with 9 steps
1.1: 66 percent / LiCl; water / dimethylsulfoxide / 4 h / 160 °C
2.1: 68 percent / diisobutylaluminum hydride / toluene; tetrahydrofuran / 4 h / -78 °C
3.1: phenylsilane; Pd(PPh3)4 / CH2Cl2 / 0.75 h
4.1: 1.10 g / Et3N / CH2Cl2 / 0.75 h
5.1: H2; HCl / Pd/C / diethyl ether; methanol / atmospheric pressure
6.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH2Cl2 / 0.5 h / 20 °C
6.2: 550 mg / triethylamine / CH2Cl2 / 4 h / 20 °C
7.1: 63 percent / imidazole / CH2Cl2 / 2 h
8.1: piperidine / tetrahydrofuran; acetonitrile / 2.5 h / 20 °C
9.1: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; triethylamine / CH2Cl2 / 0.5 h / 20 °C
9.2: 20.0 mg / triethylamine / CH2Cl2; tetrahydrofuran / 14 h / 20 °C
With
piperidine; 1H-imidazole; hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); phenylsilane; water; hydrogen; diisobutylaluminium hydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1021/ja057664z