Multi-step reaction with 13 steps
1.1: 95 percent / Ac2O / 0.02 h / microwave irradiation
2.1: 80 percent / NaBH4 / tetrahydrofuran / 16 h / 20 °C
3.1: aq. Cs2CO3 / acetone / 3 h / Heating
3.2: 60 percent / dimethylformamide / 24 h / 20 °C
4.1: 95 percent / DIEA; DMAP / dimethylformamide / 24 h / 20 °C
5.1: 100 percent / H2 / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr
6.1: 100 percent / pyridine / dimethylformamide / 0.75 h / 20 °C
7.1: 70 percent / DIEA; DMAP / dimethylformamide / 16 h / 20 °C
8.1: 92 percent / H2 / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr
9.1: 95 percent / pyridine / dimethylformamide / 0.75 h / 20 °C
10.1: 50 percent / DIEA; DMAP / dimethylformamide / 16 h / 20 °C
11.1: 92 percent / H2 / Pd/C / ethyl acetate / 1 h / 20 °C / 2280 Torr
12.1: 95 percent / pyridine / dimethylformamide / 0.75 h / 20 °C
13.1: 50 percent / DIEA; DMAP / dimethylformamide / 16 h / 20 °C
With
pyridine; dmap; sodium tetrahydroborate; hydrogen; acetic anhydride; caesium carbonate; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1039/b405856a