Multi-step reaction with 5 steps
1: 1.) lithium diethylamide / 1.) THF, hexane, 40 min; other reagents: lithium diisopropylamide, lithium hexamethyldisilazide, dimethylpropyleneurea presence or absence, 2.) THF, hexane, 2 deg C, overnight
2: 1.0 g / LiOH*H2O / tetrahydrofuran; H2O / 25 °C
3: 99 percent / diisopropylethylamine, HOAt, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate / CH2Cl2 / 1 h / 25 °C
4: HBr, AcOH / CH2Cl2 / 1 h / 25 °C
5: 0.72 g / diisopropylethylamine, HOAt, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate / CH2Cl2 / 72 h / 25 °C
With
lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate; lithium diethylamide; hydrogen bromide; acetic acid; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo952285h