Multi-step reaction with 7 steps
1: 94 percent / H2 / 5percent Rh/alumina / methanol / 16 h / 2585.7 Torr
2: 1.) imidazole, phenyl dichlorophosphate / 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, overnight
3: 1.) secondary butyllithium / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, 0 deg C, 1 h
4: 95 percent / NaBH4 / tetrahydrofuran; methanol / 1.5 h / 0 °C
5: trifluoroacetic acid / CH2Cl2 / 2 h / Ambient temperature
6: 16 percent / H2 / 5percent Rh/alumina / ethyl acetate / 4 h / 1551.4 Torr
7: 98 percent / 1 M BBr3 / CH2Cl2 / 2 h / Ambient temperature
With
1H-imidazole; sodium tetrahydroborate; hydrogen; sec.-butyllithium; boron tribromide; O-phenyl phosphorodichloridate; trifluoroacetic acid;
Rh/Al2O3;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate;