Multi-step reaction with 11 steps
1: SOCl2 / 1 h / 75 °C
2: CH2Cl2 / 1 h / Ambient temperature
3: H2 / Pd/C / ethyl acetate / 20 h / 760 Torr
4: 96 percent / Heating
5: Et3N / 1 h / 0 - 20 °C
6: 1.) BuLi / 1.) THF, -40 deg C - -50 deg C, 1 h, 2.) THF, -50 deg C, - RT
7: 0.4 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature
8: tetrahydrofuran; diethyl ether
9: 70 percent / NaBH4 / dioxane; H2O / 20 h / Ambient temperature
10: 63 percent / DMSO, TFAA / CH2Cl2 / 3 h
11: 77 percent / benzene / 20 h / 80 °C
With
sodium tetrahydroborate; sodium amalgam; n-butyllithium; thionyl chloride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1021/jm00051a005