Multi-step reaction with 8 steps
1: 94 percent / 4-methylmorpholine, 1-hydroxybenzotriazole hydrate, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 2 h
2: 1.) DMSO, oxalyl chloride, 2.) TEA / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to 0 deg C
3: TFA / CHCl3 / 144 h / Heating
4: 319 mg / TiCl4 / CH2Cl2 / 28 h
5: diethyl ether; methanol; CH2Cl2 / 0.17 h / 0 °C
6: 95 percent / H2 / 10percent Pd/C / ethyl acetate / 3.5 h / Ambient temperature
7: hydrazine monohydrate / methanol / 48 h / Ambient temperature
8: TEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) RT, 2 h
With
4-methyl-morpholine; oxalyl dichloride; TEA; hydrogen; titanium tetrachloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; hydrazine hydrate; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm950677a