Multi-step reaction with 11 steps
1: 96 percent / LiAlH4 / diethyl ether / 14 h / Ambient temperature
2: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH2Cl2 / 1.5 h / Ambient temperature
3: 80 percent / NaI / butan-2-one / 5.5 h / 75 °C
4: 1) (2-thienyl)Cu(CN)Li / 1) THF, a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, 2) a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, c) room temp., 18 h
5: 90 percent / Zn dust, AcOH / H2O; tetrahydrofuran / 2.5 h / 60 °C
6: 79 percent / 3.5 N Na2CO3 / CH2Cl2 / 1) 0 deg C, 30 min, 2) room temp., 2.5 h
7: 91 percent / O2 / PdCl2, CuCl2 / dimethylformamide; H2O / 50 °C
8: H2 / 10percent Pd/C / methanol / 0.5 h
9: H2, 10percent HCl / 10percent Pd/C / methanol / 2 h
10: Na2CO3 / dimethylformamide / 6 h / 70 °C
11: 76 percent / Et3N / CH2Cl2 / 0.17 h / -20 °C
With
hydrogenchloride; dmap; lithium aluminium tetrahydride; hydrogen; oxygen; sodium carbonate; acetic acid; thien-2-yl(cyano)copper lithium; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc;
palladium on activated charcoal; copper dichloride; palladium dichloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; butanone;
DOI:10.1016/S0040-4020(01)80881-4