Multi-step reaction with 8 steps
1: 82 percent / p-toluenesulfonic acid monohydrate / benzene / 6 h / Heating
2: 93.5 percent / 0.5 N NaOH / acetonitrile / 18 h / Ambient temperature
3: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h
4: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr
5: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h
6: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C
7: sodium dithionite / dimethylformamide; H2O / 0.5 h
8: 0.1N NaOH / 1.5 h
With
4-methyl-morpholine; hydrogenchloride; sodium hydroxide; sodium dithionite; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; isobutyl chloroformate;
palladium on activated charcoal;
In
methanol; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jm00141a010