Multi-step reaction with 17 steps
1.1: sodium tetrahydroborate / tetrahydrofuran; water / -20 °C
2.1: hydrogen / Raney nickel / ethanol; water / 1 h / 2844.39 Torr
3.1: dichloromethane / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C
5.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 0 - 20 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C
7.1: borane / tetrahydrofuran / -30 - 0 °C
7.2: -10 - 0 °C
8.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 0 °C
9.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h
10.1: sodium acetate / 85 - 90 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
12.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C
13.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 20 °C / Neat (no solvent)
14.1: hydrogen / palladium 10% on activated carbon / methanol; ethyl acetate / 3 h / 2585.81 Torr
15.1: 4-methyl-morpholine; HATU / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C
16.1: hydrogen / palladium 10% on activated carbon / methanol; ethyl acetate / 3 h / 2585.81 Torr
17.1: 4-methyl-morpholine; HATU / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C
With
4-methyl-morpholine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; borane; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU;
dmap; palladium 10% on activated carbon;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; benzene;