Multi-step reaction with 11 steps
1: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min
2: H2 / 10percent Pd/C / methanol
3: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min
4: H2 / 10percent Pd/C / methanol
5: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min
6: H2 / 10percent Pd/C / methanol
7: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min
8: H2 / 10percent Pd/C / methanol
9: 72 percent / N-methylmorpholine / dioxane / 0.33 h / Ambient temperature
10: H2 / 10percent Pd/C / methanol / 1 h
11: 37 percent / CaCO3 / N,N-dimethyl-acetamide / 60 h / Ambient temperature
With
4-methyl-morpholine; hydrogen; calcium carbonate; isobutyl chloroformate;
palladium on activated charcoal;
In
1,4-dioxane; methanol; N,N-dimethyl acetamide;
DOI:10.1021/jm00121a029