Multi-step reaction with 11 steps
1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C
2: hydrogenchloride / ethyl acetate / 3 h / 20 °C
3: triethylamine / toluene / 18 h / 90 °C
4: palladium 10% on activated carbon; hydrogenchloride; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr
5: sodium hydrogencarbonate / tetrahydrofuran / 18 h / 20 °C
6: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 50 °C
7: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
8: hydrogenchloride / ethyl acetate; methanol / 3 h / 20 °C
9: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
10: hydrogenchloride / ethyl acetate / 3.5 h / 20 °C
11: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 3 h / 20 °C
With
hydrogenchloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU;
In
tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2013.07.020