Multi-step reaction with 12 steps
1: 89 percent / sodium, methanol
2: 11 percent / imidazole / dimethylformamide / 0.67 h / 0 °C
3: sodium hydride / tetrahydrofuran; dimethylformamide / 0.75 h / 0 °C
4: methanol / 4 h / 40 °C
5: 96 percent / sodium hydride / dimethylformamide / 1 h
6: 69 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2 h, 2) 1,4-dioxane, 1 h, 80 deg C
7: 81 percent / oxalyl bromide / 1,2-dichloro-ethane; dimethylformamide / 1.5 h / 0 °C
8: 1) silver silicate, acetivated powdered 4 Angstroem molecular sieves, 2) Bu4NF / 1) 1,2-dichloroethane, -20 deg C, 1 h, 2) THF, 1 h, 0 deg C
9: pyridinium dichromate / dimethylformamide / 20 h
10: 1,2-dichloro-ethane; diethyl ether
11: 76 percent / 24 h / Ambient temperature
12: 1) trifluororacetic acid (85percent), 2) pyridine / 1) water, 30 min, room temperature, 2) overnight
With
pyridine; 1H-imidazole; methanol; dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; Oxalyl bromide; silver silicate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium; sodium hydride; trifluoroacetic acid; sodium nitrite;
In
tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(90)84259-W