Multi-step reaction with 8 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C
1.2: 2 h / 25 - 40 °C / Cooling with ice
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -30 - -10 °C / Inert atmosphere
2.2: 2 h / -30 - -10 °C / Inert atmosphere
2.3: 10.5 h / 20 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 14 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
5.1: sodium carbonate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / water; 1,4-dioxane / 2 h / 95 °C / Inert atmosphere
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 20 °C
7.1: sodium periodate / tetrahydrofuran; water / 24 h / 20 °C
8.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
With
sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium carbonate; benzotriazol-1-ol; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;