Multi-step reaction with 8 steps
1: conc. H2SO4 / CH2Cl2
2: 89.7 percent / 0.25 N NaOH / tetrahydrofuran / 25 °C
3: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, 2.) THF, DMF
4: 86.5 percent / ammonium formate, H2 / 10percent Pd/C / methanol / 0.67 h
5: 89.7 percent / N,N-diisopropylethylamine / toluene / 2.25 h / Heating
6: 85.9 percent / 0.25 N NaOH / tetrahydrofuran / 25 °C
7: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 to -20 deg C, 1 h, 2.) THF, DMF, 25 deg C, 1 h
8: 88.3 percent / anisole / CH2Cl2 / 3.25 h / 25 °C
With
4-methyl-morpholine; sodium hydroxide; sulfuric acid; hydrogen; ammonium formate; methoxybenzene; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jm00390a005