Multi-step reaction with 9 steps
1: 80 percent / NaHCO3 / acetonitrile / 24 h / Heating
2: H2 / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr
3: 1.) pyridine, TsCl, 2.) NaHCO3 / 1.) CH2Cl2, 1 h, 2.) 1 h
4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h
5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h
6: 90 percent / NaBH4 / methanol / 0.05 h / -25 °C
7: Et3N / CH2Cl2 / 0.5 h / 0 °C
8: 55 percent / DBU / 1 h / 100 °C
9: aq. NaOH / methanol; tetrahydrofuran / 12 h
With
pyridine; sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo00208a017