Multi-step reaction with 11 steps
1.1: 98 percent / imidazole / CH2Cl2 / 20 °C
2.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 2.5 h / -78 °C
2.2: 67 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C
3.1: lithium; EtNH2 / tetrahydrofuran / 4 h / -78 °C
4.1: 3.97 g / Et3N / dioxane; H2O / 20 °C
5.1: 91 percent / (dimethylamino)pyridine; pyridine / 20 °C
6.1: 73 percent / TBAF / tetrahydrofuran / 20 °C
7.1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C
8.1: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C
9.1: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C
10.1: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C
11.1: 97 percent / NaOH; MeOH / 20 °C
With
pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; ammonia; lithium; ethylamine; triethylamine; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water;
3.1: Birch reduction / 7.1: Mitsunobu reaction;
DOI:10.1021/jo034828q