Multi-step reaction with 7 steps
1: 1) N-methylmorpholine, iBuOCOCl / 1) CH2Cl2, 0 deg C, 15 min, 2) CH2Cl2, reflux, 20 min, r.t., overnight
2: NH3, HgCl2 / tetrahydrofuran / 3 h / 0 °C
3: 64 percent / NH4OAc / acetic acid / Ambient temperature
4: 97 percent / 33percent HBr / acetic acid / 1) 0 deg C, 10 min, 2) 25 deg C, 30 min
5: 96 percent / pyridine / 1) 0 deg C, 15 min, 2) reflux, 1.5 h
6: 88 percent / K2CO3 / dimethylformamide / 2 h / 25 °C
7: 85 percent / NEt3, 97percent HCOOH / 5percent Pd/C / acetonitrile / Heating
With
4-methyl-morpholine; pyridine; formic acid; ammonium acetate; ammonia; hydrogen bromide; potassium carbonate; triethylamine; mercury dichloride; isobutyl chloroformate;
palladium on activated charcoal;
In
tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0223-5234(98)80048-2