Multi-step reaction with 8 steps
1: 87.5 percent / dicyclohexylcarbodiimide, 4-dimethylaminopyridine / CH2Cl2 / 1. 5 min, 0 deg C 2. 5.5 h, room temperature
2: 80 percent / BF3*Et2O / CH2Cl2 / 1. -10 deg C to 0 deg C, 2 h 2. 0 deg C, 7 h
3: 81 percent / tetrahydrofuran; dimethylformamide; paraffin; xylene / 20 h / 1. -80 deg C to -75 deg C, 90 min, 2. to room temperature, 2 h 3. room temperature
4: 1. n-butyllithium / 1. DME, hexane, -78 deg C, 75 min 2. 10 deg C, 23 h
5: 92 percent / H2 / NaBH4, Ni(Ac)2*4H2O, ethylene diamine / ethanol / 2 h
6: 73 percent / NEt3 / diethyl ether / 0 °C
7: 86 percent / NaI, K2CO3 / acetone / 168 h / 35 °C
8: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C
With
dmap; n-butyllithium; hydrogen; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; sodium iodide;
sodium tetrahydroborate; boron trifluoride diethyl etherate; nickel diacetate; ethylenediamine;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; paraffin; xylene;