Multi-step reaction with 5 steps
1: 98 percent / Et3N / CH2Cl2 / 3.5 h / -50 - 20 °C
2: 1.) n-BuLi, i-Pr2NH, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone / 1.) THF, hexane, -60 deg C, 1.5 h, 2.) THF, hexane, a.) -60 deg C, 1 h, b.) RT, 1 h
3: 100 percent / H2 / 5percent Pd/C / ethanol / 24 h / 760 Torr / Ambient temperature
4: 92 percent / LiAlH4 / diethyl ether / 6 h / Heating
5: 1.) 1,1'-carbonyldiimidazole / 1.) CH2Cl2, RT, 1.5 h, 2.) CH2Cl2, RT, 22 h
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; n-butyllithium; hydrogen; triethylamine; diisopropylamine; 1,1'-carbonyldiimidazole;
palladium on activated charcoal;
In
diethyl ether; ethanol; dichloromethane;
DOI:10.1021/jm00081a009