Multi-step reaction with 13 steps
1: 72.8 percent / sodium borohydride / ethanol / 2 h / 20 °C
2: 95.3 percent / H2 / 5percent palladium-carbon / methanol / 24 h / Ambient temperature
3: dimethylsulfoxide / 4.5 h / 190 °C
4: 62.7 percent / diethyl ether / 3 h / Ambient temperature
5: 97.1 percent / potassium carbonate / methanol / 4 h / 0 °C
6: 14.7 percent / diisobutylaluminium hydride / hexane; toluene / 2 h / -60 °C
8: 1) 50percent sodium hydride / 1) benzene, 10 min, RT, 2) benzene, 2 h, RT
9: 100 percent / sodium borohydride / methanol / 1 h / 0 °C
10: 100 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 0 °C
11: 98 mg / diisobutylaluminium hydride / toluene / 4 h / -60 °C
13: 9 mg / acetic acid; H2O; tetrahydrofuran / 2.5 h / 40 °C
With
sodium tetrahydroborate; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; toluene;
DOI:10.1248/cpb.30.796