Multi-step reaction with 13 steps
1: 1.) n-BuLi / 1.) THF, -30 deg C, 2 h, 2.) THF, -25 deg C, 15 h
2: 88 percent / MeI, CaCO3, H2O / acetonitrile / 16 h
3: 95 percent / NaBH4, Et2BOMe / tetrahydrofuran; methanol / 3 h / -78 °C
4: 90 percent / PPTS / CH2Cl2 / 0.33 h
5: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 0.5 h
6: 99 percent / imidazole / dimethylformamide / 3.5 h
7: 81 percent / Li, NH3 (liq.) / tetrahydrofuran; propan-2-ol / 0.25 h / -70 °C
8: Py / 2.5 h / 0 °C
9: t-BuOK / diethyl ether; methanol / 1.5 h
10: 1.) n-BuLi / 1.) THF, -30 deg C, 2 h, 2.) THF, -25 deg C, 15 h
11: 68 percent / MeI, CaCO3, H2O / acetonitrile / 16 h
12: Me4NBH(OAc)3, AcOH / acetonitrile / 20 h / -25 °C
13: 100 percent / PPTS / CH2Cl2 / 0.67 h
With
pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; potassium tert-butylate; ammonia; water; hydrogen; pyridinium p-toluenesulfonate; lithium; acetic acid; calcium carbonate; tetramethylammonium triacetoxyborohydride; methyl iodide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;
DOI:10.3987/COM-92-6041