Multi-step reaction with 13 steps
1: 97 percent / potassium hydride, 1,3-diaminopropane / 18 h / Ambient temperature
2: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature
3: 93 percent / (Ph3P)2PdCl2, Et3N, CuI / 4 h / 50 °C
4: H2 / 5percent Pd/C / ethanol; ethyl acetate / 4 h
5: tetrabutylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature
6: 90 percent / triphenylphosphine, imidazole, I2 / toluene / 0.5 h / 65 °C
7: K2CO3 / dimethylformamide / 1 h / 90 °C
8: toluene / 1 h / 50 °C
9: 85percent MCPBA / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 16 h
10: trifluoroacetic anhydride / dimethylformamide / 16 h / Ambient temperature
11: thionyl chloride / toluene / 1.5 h / 0 - 20 °C
12: K2CO3 / dimethylformamide / 1 h / 90 °C
13: MCPBA / CH2Cl2 / 1.5 h / 0 °C
With
1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hydride; potassium carbonate; Trimethylenediamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00074a013