Multi-step reaction with 8 steps
1: 1.) pyridine, room temp., 5 h, 2.) pyridine, room temp., overnight
2: CF3COOH / CH2Cl2 / 1 h / Ambient temperature
3: 1.) (COCl)2, DMSO, Et3N, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1.5 h, 2.) CH2Cl2, -78 deg C, 30 min, 0 deg C, 1.5 h
4: 72 percent / Bu4NBH3CN / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 0 deg C, 1.5 h
5: 1.) K2CO3, 2.) NH3 / 1.) MeOH, room temp., 10 min, 2.) MeOH, 10 min
6: 100 percent / pyridine / 48 h / Ambient temperature
7: 93 percent / Et3N, DMAP / toluene / 15 h / Ambient temperature
8: 91 percent / Bu3SnH, AIBN / toluene / 4 h / 110 °C
With
dmap; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; tetrabutylammonium (cyano)trihydroborate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; pyridine; dichloromethane; toluene;
DOI:10.1021/jo971703a