Multi-step reaction with 10 steps
1: 69 percent / p-toluenesulfonic acid / dimethylformamide / 1 h / 60 °C / reduced pressure
2: 94 percent / NaH / dimethylformamide / 1 h / 0 °C
3: 1) borane-trimethylamine complex, molecular sieves (4 Angstroem), 2) AlCl3 / 1) THF, 1 h, 2) 0 deg C, 3 h
4: 99 percent / pyridine / 16 h / Ambient temperature
5: 57 percent / molecular sieves (4 Angstroem), methyl triflate / diethyl ether / 18 h
6: 98 percent / NaOMe / methanol / pH 10, overnight
7: 73 percent / molecular sieves (4 Angstroem), trimethylsilyl triflate / CH2Cl2 / -30 °C
8: 78 percent / H2SO4, acetic acid / 2 h / Ambient temperature
9: 62 percent / molecular sieves (3 Angstroem), trimethyl triflate / CH2Cl2 / 0.25 h
10: 75 percent / PdCl2, Na-acetate / acetic acid / 22 h / sonication
With
pyridine; aluminium trichloride; trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; 3 A molecular sieve; 4 A molecular sieve; sulfuric acid; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; methyl trifluoromethanesulfonate; palladium dichloride;
In
methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90498-1