Multi-step reaction with 11 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C
1.2: 2 h / 0 - 20 °C
2.1: sodium methylate / methanol / 16 h / 20 °C
3.1: ethyl acetate; diethyl ether
4.1: lithium borohydride / tetrahydrofuran / 3 h / 0 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C
7.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C
8.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 0.33 h / 0 °C
8.2: 16 h / 0 - 20 °C
9.1: copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate / butan-1-ol; ethanol; water / 20 °C
10.1: hydrogen / palladium 10% on activated carbon / methanol / 1.5 h / 2844.39 Torr
11.1: triethylamine / dichloromethane / 4 h / 0 °C
With
lithium borohydride; sodium azide; copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; hydrogen; sodium methylate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; butan-1-ol;