Multi-step reaction with 7 steps
1: 1.) Et3N, 2.) DL-camphorsulfonic acid / 1.) CH2Cl2, 0 deg C, 30 min, 2.) acetone, 25 deg C, 16 h
2: 1.) NaOMe, 2.) aq. HCl / 1.) DMF, MeOH, 60 deg C, 30 min, 2.) THF, 25 deg C, 1 h
3: 1.) t-BuLi, 2.) triisopropylborate
4: 95 percent / imidazole / dimethylformamide / 0.5 h / 25 °C
5: 100 percent / H2, quinoline / 5percent Pd(2.7percent Pb)-CaCO3 / ethanol / 0.5 h / 25 °C
6: 100 percent / aq. NaOH / tetrahydrofuran; methanol / 16 h / 25 °C
7: 100 percent / Et3N / CH2Cl2 / 1 h / 0 °C
With
1H-imidazole; quinoline; hydrogenchloride; sodium hydroxide; Triisopropyl borate; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; sodium methylate; triethylamine;
Pd(2.7 percent Pb)-CaCO3;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(97)00090-4