Multi-step reaction with 7 steps
1: 78 percent Turnov. / Li2CO3, 4 Angstroem molecular sieves / dimethylformamide / 18 h / Ambient temperature
2: 97 percent / H2 / Pd/C / methanol / 1 h / 760 Torr / Ambient temperature
3: 88 percent / DCC, DMAP / CH2Cl2 / 15 h / Ambient temperature
4: 72 percent / aq. HF / acetonitrile / 7 h / -25 - -15 °C
5: 1-hydroxybenzotriazole, N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide, N,N-diisopropylethylamine / tetrahydrofuran / 4 h / -10 - -5 °C
6: 99 percent / H2 / Pd/C / tetrahydrofuran / 3 h / 760 Torr / Ambient temperature
7: 76 percent / N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide, 1-hydroxy-7-azabenzotriazole, N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature
With
dmap; 1-hydroxy-7-aza-benzotriazole; 4 A molecular sieve; N-<(1H-benzotriazol-1-yl)(dimethylamino)methylene>-N-methylmethanaminium hexafluorophosphate N-oxide; N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexafluorophosphate N-oxide; hydrogen fluoride; hydrogen; lithium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo961932h