Multi-step reaction with 14 steps
1: 12 percent / tetrahydrofuran / -50 °C
2: H2 / Pd/C / ethyl acetate; methanol / 24 h / 735.5 Torr / Ambient temperature
3: DMSO, (COCl)2, Et3N / CH2Cl2 / 1) 30 min, -70 deg C 2) 30 min, r.t.
4: K2CO3 / methanol / 5 h / Ambient temperature
5: NaBH4 / aq. ethanol / 10 h / Ambient temperature
6: pyridine / CH2Cl2 / 8 h / 0 °C
7: 70percent AcOH / methanol / 7 h / Ambient temperature
8: 81 percent / K2CO3 / methanol / 12 h / Ambient temperature
9: 95 percent / POCl3, PPTS / diethyl ether / 1 h
10: 88 percent / CuBr / tetrahydrofuran / -30 deg C to r.t.
11: 87 percent / imidazole / dimethylformamide / 12 h / Ambient temperature
12: 84 percent / 0.5N HCl / 1) 30 min, 0 deg C 2) 30 min, r.t.
13: 86 percent / pyridine / 6 h / Ambient temperature
14: 90 percent / (t-Bu4N)F / tetrahydrofuran / 2 h / Ambient temperature
With
pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; dimethyl sulfoxide; tetra(tert-butyl)-ammonium fluoride; triethylamine; copper(I) bromide; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)92629-7