Multi-step reaction with 11 steps
1: CH2Cl2 / 1 h / Ambient temperature
2: H2 / Pd/C / ethyl acetate / 20 h / 760 Torr
3: 96 percent / Heating
4: Et3N / 1 h / 0 - 20 °C
5: 1.) BuLi / 1.) THF, -40 deg C - -50 deg C, 1 h, 2.) THF, -50 deg C, - RT
6: 1.5 g / sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature
7: tetrahydrofuran; diethyl ether
8: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 40 min, b.) 1 h
9: 93 percent / NaBH4 / ethanol / 0.25 h / Ambient temperature
10: Et3N / CH2Cl2 / 20 h
11: 93 percent / BuLi / tetrahydrofuran / 3 h / -78 °C
With
sodium tetrahydroborate; sodium amalgam; n-butyllithium; hydrogen; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate;
DOI:10.1021/jm00051a005