Multi-step reaction with 10 steps
1.1: 81 percent / imidazole / dimethylformamide / 0 - 20 °C
2.1: 87 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 0 °C
3.1: 99 percent / Et3N / CH2Cl2 / 1 h / 20 °C
4.1: O3; NaHCO3 / CH2Cl2 / 0.33 h / -78 °C
4.2: Me2S / CH2Cl2 / -78 - 20 °C
5.1: NH2OH*HCl; Et3N / 11 h / 20 °C
6.1: H2 / PdCl2 / methanol; CH2Cl2 / 12 h / 20 °C
7.1: 410 g / Et3N / CH2Cl2 / 10 h / 20 °C
8.1: NaH / tetrahydrofuran / 0.33 h / 0 °C
8.2: 92 percent / tosylimidazole / tetrahydrofuran / 12 h / 20 °C
9.1: KH / dimethylformamide / 0.5 h / 0 °C
9.2: 69 percent / dimethylformamide / 16 h / 80 °C
10.1: 98 percent / Dess-Martin periodinane / CH2Cl2 / 17 h / 20 °C
With
1H-imidazole; hydroxylamine hydrochloride; water; hydrogen; potassium hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium dichloride;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
10.1: Dess-Martin oxidation;
DOI:10.1021/jm010448q