Multi-step reaction with 9 steps
1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 deg C, 5 min, 2.) -15 deg C, 0.5 h; 25 deg C
2: 96 percent / hydrogen, formic acid / Pd black / methanol / 0.25 h
3: CF3CO2H / CH2Cl2 / 0.5 h / 25 °C
4: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 deg C, 5 min, 2.) -15 deg C, 0.5 h; 25 deg C
5: N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 18 h
6: triethylamine / dimethylformamide / 4 h / 40 °C
7: N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 18 h
8: CF3CO2H / CH2Cl2 / 0.5 h / 25 °C
9: pyridine / tetrahydrofuran / 24 h / 25 °C
With
4-methyl-morpholine; pyridine; formic acid; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate;
palladium;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00414a075