Multi-step reaction with 8 steps
1: 1.) n-butyllithium, diisopropylamine / 1.) hexane, THF, -78 deg C, 15 min, 2.) THF, -78 deg C to 0 deg C, 1h
2: 98 percent / p-TSA, MgSO4 / toluene; CHCl3 / 3 h / 70 °C
3: 100 percent / H2 / Lindlar / toluene; CHCl3 / 12 h / 760 Torr
4: tert-butylamine-borane complex / CH2Cl2 / 1 h / Heating
5: 92 percent / pyridine, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 0.2 h / 0 °C
6: 96 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1.) room temp., overnight, 2.) reflux, 30 min
7: 98 percent / tributylamine, 98percent formic acid / Pd(OAc)2(Ph3P)2 / dimethylformamide / 0.5 h / 70 °C
With
pyridine; dmap; n-butyllithium; formic acid; 2,6-di-tert-butyl-4-methylpyridine; tributyl-amine; hydrogen; borane tert-butylamine; magnesium sulfate; toluene-4-sulfonic acid; diisopropylamine;
Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate;
In
dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00183a042