Multi-step reaction with 14 steps
1.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C
2.1: pyridine-SO3 complex; triethylamine / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C
3.1: triethylamine / 12 h
3.2: 1 h / -78 °C
3.3: 1 h / -78 °C
4.1: / acetonitrile / 40 °C
4.2: 16 h / 20 °C / Neat (no solvent)
5.1: hydrogen / ethanol / 1.5 h / 2585.81 Torr
6.1: triethylamine / dichloromethane / 0 - 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 45 °C
8.1: dmap / dichloromethane / 0 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0 - 20 °C
12.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 2585.81 Torr
13.1: triethylamine / dichloromethane / 0.5 h / 0 °C
14.1: triethylamine / dichloromethane / 0 - 20 °C
With
lithium borohydride; pyridine-SO3 complex; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid;
dmap; palladium 10% on activated carbon;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;