Multi-step reaction with 9 steps
1: 93.2 percent / K2CO3 / acetone / 18 h / Heating
2: 62 percent / NaN3, NH4Cl / dimethylformamide / 24 h / 110 °C
3: 67 percent / K2CO3 / acetonitrile / 1 h / Heating
4: 96 percent / BBr3 / CH2Cl2
5: 84 percent / Ph3P, DEAD / CH2Cl2 / 12 h
6: 37.5 percent / triethylamine / CHCl3 / 18 h / Heating
7: 86.2 percent / LAH / tetrahydrofuran / 0.5 h / Ambient temperature
8: 92.2 percent / Br2, Ph3P / CH2Cl2 / 0.17 h
9: 1.) N-isopropylcyclohexylamine, n-butyllithium / 1.) THF, hexane, 30 min, 2.) THF, hexane, DMSO, RT, 1 h
With
lithium aluminium tetrahydride; n-butyllithium; sodium azide; N-cyclohexylisopropylamine; bromine; boron tribromide; potassium carbonate; ammonium chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jm00074a004