Multi-step reaction with 11 steps
1: lithium diisopropyl amide / tetrahydrofuran; acetone / 2 h / -78 °C / Inert atmosphere
2: triethylamine; Methanesulfonic anhydride / dichloromethane / 40 h / 20 °C
3: osmium(VIII) oxide / water; acetone / 17 h / 20 °C
4: triethylamine / dichloromethane / 0.67 h / 0 °C
5: sodium azide; ammonium chloride / ethanol / 20 h / 80 °C
6: triethylamine / dichloromethane / 2 h / 0 - 20 °C
7: triphenylphosphine; citric acid / water; tert-butyl methyl ether; tetrahydrofuran / 0.5 h / 20 °C
8: 4-methyl-morpholine; aluminum oxide / water; tetrahydrofuran / 1.5 h / 20 °C
9: N,N-dimethyl-formamide / 3 h / 20 °C
10: ammonia / methanol / 44 h / 55 °C / Sealed vial
11: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.5 h / 0 - 20 °C
With
4-methyl-morpholine; aluminum oxide; osmium(VIII) oxide; sodium azide; ammonia; ammonium chloride; triethylamine; triphenylphosphine; trifluoroacetic anhydride; citric acid; lithium diisopropyl amide; Methanesulfonic anhydride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; tert-butyl methyl ether; water; N,N-dimethyl-formamide; acetone;