Multi-step reaction with 7 steps
1.1: N,N,N',N'-tetramethylenediamine; sec-butyllithium / diethyl ether; cyclohexane / 4.5 h / -78 °C
1.2: 73 percent / diethyl ether; cyclohexane / -78 - 20 °C
2.1: 82 percent / N,N-diisopropylethylamine; TBTU / acetonitrile / 20 °C
3.1: 95 percent / HCl / methanol; dioxane / 2 h / Heating
4.1: 47 percent / toluene / 60 h / Heating
5.1: 69 percent / BH3*SMe2 / tetrahydrofuran / 16 h / Heating
6.1: ethanol / 0.17 h / 20 °C
6.2: 71 percent / BH3*pyridine / ethanol / 18 h / 20 °C
7.1: 72 percent / triethylamine / CH2Cl2 / 0 - 20 °C
With
hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; sec.-butyllithium; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; toluene; acetonitrile;
DOI:10.1021/jm0604878