Multi-step reaction with 9 steps
1: 1.) NaH / 1.) DMF, 30 deg C, 2-3 h; 2.) hexane, room temp., 2 h
2: 1.) n-BuLi, TMEDA / 1.) hexane, 0 - 4 deg C, 1 h; 2.) 1 h
3: 38 percent / HCl, p-toluenesulfonic acid / methanol; H2O / Ambient temperature; 1.) 0.5 h, room temp.; 2.) reflux, 3 h
4: 78 percent / KF / dimethylformamide / Ambient temperature
5: 1.) 1-chloro-N,N,2-trimethyl propenylamine; 2.) NaH / 1.) CH2Cl2, room temp., 30 min; 2.) ether, overnight, room temp.
6: 49 percent / Zn/HCl / tetrahydrofuran / 1 h
7: 1-chloro-N,N,2-trimethylpropenylamine / CH2Cl2 / 0.5 h / Ambient temperature
8: 2.2 g / NaH / diethyl ether / Ambient temperature
9: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature
With
hydrogenchloride; potassium fluoride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydrogen; sodium hydride; toluene-4-sulfonic acid; zinc;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)90268-6