Multi-step reaction with 11 steps
1.1: 97 percent / pTsOH*H2O / dimethylformamide / 1 h / 20 °C
2.1: 95 percent / DIBAL / CH2Cl2 / 2 h / 0 °C
3.1: 96 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C
4.1: 74 percent / NaH / dimethylformamide / 20 h / 20 °C
5.1: [C8H12Ir(PMePh2)2]PF6; H2 / tetrahydrofuran / 3 h / 20 °C
5.2: 65 percent / I2; water; pyridine / 12 h / 20 °C
6.1: 88 percent / DBU / CH2Cl2 / 1 h / 0 °C
7.1: 93 percent / 4A MS / CH2Cl2 / 1 h / 20 °C
8.1: PPh3; NH3 / tetrahydrofuran; H2O / 24 h / 60 °C
9.1: 74 percent / DCC; DMAP / CH2Cl2 / 2 h / 20 °C
10.1: HCl; water / dioxane / 3 h / 60 °C
10.2: 26 percent / dimethylformamide / 1 h / 60 °C
11.1: 62 percent / DMAP / CH2Cl2 / 3 h / 20 °C
With
hydrogenchloride; dmap; [C8H12Ir(PMePh2)2]PF6; ammonia; water; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00055-6