Multi-step reaction with 10 steps
1: 92.9 percent / NaBH4 / methanol / 1 h / 10 °C
2: Et3N / CH2Cl2
3: 95.1 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature
4: 95.1 percent / N-bromosuccinimide / ethanol
5: 77.2 percent / Fe, HCl / methanol / 0.5 h / Heating
6: 95 percent / 4-(dimethylamino)pyridine, pyridine, N-methylpyrrolidine / 2 h / 50 °C
7: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 30 min
8: 95.8 percent / H2NNH2*H2O / ethanol / 1 h / Heating
9: 67.4 percent / pyridine / 6 h / 90 °C
10: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 30 min
With
1-Methylpyrrolidine; pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; N-Bromosuccinimide; iron; sodium hydride; potassium carbonate; hydrazine hydrate; triethylamine;
In
methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm970591c