Multi-step reaction with 9 steps
1: 51 percent / TEA, trifluoroacetic anhydride / CH2Cl2 / 12 h / 0 °C
2: 66 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 70 °C
3: 1) NaIO4, 2) NaBH4 / 1) 2-butanol, water, 2 h, RT, 2) THF, 0 deg C, 1 h
4: 92 percent / N,N-diethylaniline / CH2Cl2 / 24 h / Ambient temperature
5: 80 percent / H2 / 5percent Pd-C / ethyl acetate / 4 h / 760 Torr / Ambient temperature
6: 88 percent / acetic anhydride / 8 h / Ambient temperature
7: 80 percent / POCl3, 2,6-lutidine / CH2Cl2 / Ambient temperature; 1) 4 h, 2) 8 h
8: 95 percent / tributyltin hydride, α,α'-azobis-isobutyronitril / benzene / 0.5 h / 80 °C
9: 86 percent / 10percent aq. HCl / methanol / 3 h / 70 °C
With
2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; TEA; azobisisobutyronitrile; hydrogen; tri-n-butyl-tin hydride; acetic anhydride; toluene-4-sulfonic acid; N,N-diethylaniline; trifluoroacetic anhydride; trichlorophosphate;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1248/cpb.38.1601