Multi-step reaction with 10 steps
1: 1.) N-methylmorpholine, i-butyl-chloroformiate 2.) Ag-benzoate 3.) Ag-benzoate, triethylamine / 1.) ethyleneglycol dimethylether, 5 min, 0 deg C, 2.) ether, 0 deg C, 20 min, 3.) MeOH, 30 min, RT
2: 95 percent / diisopropylethylamine, 4-(N,N-dimethyl)-amino-pyridine, N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 0 deg C, then RT, 4h
3: LiAlH4 / ether, 0 deg C, 30 min
4: benzene / 1 h / Ambient temperature
5: 83 percent / 2 N NaOH / methanol; H2O / 2 h / 30 °C
6: 73 percent / H2 / 10percentPd/C / ethyl acetate / 1 h / 3677.5 Torr / Ambient temperature
7: 1.) trifluoroacetic acid 2.) N,N-diisopropylethylamine / 1.) 30 min, RT, 2.) DMF, 2 h, RT
8: 1.) diethylamine 2.) iisopropylethylamine, benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate / 1.) MF, 20 min, RT, 2.) DMF, 4 h, RT
9: 85 percent / H2 / 10percent Pd/C / dimethylformamide; ethanol / Ambient temperature
10: 50 percent / SO3-pyridine complex / pyridine; dimethylformamide / Ambient temperature
With
4-methyl-morpholine; dmap; sodium hydroxide; lithium aluminium tetrahydride; pyridine-SO3 complex; hydrogen; silver benzoate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate;
palladium on activated charcoal; 10% palladium on active carbon;
In
pyridine; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)86144-5