Multi-step reaction with 11 steps
1: sodium / methanol / 2 h / 20 °C
2: 1.03 g / p-toleunesulfonic acid / acetonitrile / 15 h / 60 °C
3: 65 percent / NaH / dimethylformamide / 20 °C
4: 82 percent / sodium cyanoborohydride; 4A molecular sieves; trifluoroacetic acid / dimethylformamide / 12 h / 20 °C
5: 88 percent / 4A molecular sieves; N-iodosuccinimide; silver triflate / CH2Cl2 / 0 °C
6: 77 percent / sodium / methanol / 48 h / 20 °C
7: 35 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 0 °C
8: 59 percent / DDQ / CH2Cl2 / 2 h / 20 °C
9: ethylenediamine / 2-methyl-propan-2-ol / 30 h / 90 °C
10: 70 mg / triethylamine / methanol / 2 h / 20 °C
11: 98 percent / 1,2,4-triazole / CH2Cl2 / 15 h
With
1,2,4-Triazole; N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; ethylenediamine; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0008-6215(02)00178-7