Multi-step reaction with 5 steps
1: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, hexane, -78 deg C, 1 h, 2.) toluene, hexane, from -78 deg C to RT, 2.5 h
2: 1.) nBuLi, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, 4.5 h
3: 98 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature
4: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight
5: 85 percent / H2 / Pd/BaSO4 / pyridine / 36 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen; lithium diisopropyl amide;
Pd-BaSO4;
In
tetrahydrofuran; pyridine;
DOI:10.1248/cpb.46.1770