Multi-step reaction with 12 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 24 h / 90 °C
2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: sodium methylate / tetrahydrofuran; methanol / 16 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.2: 0.17 h / 0 °C
5.1: triethylamine / dichloromethane / 20 °C
6.1: N-Bromosuccinimide / tetrachloromethane / 1 h / Reflux
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C
7.2: 0.5 h / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C
9.1: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / 1,4-dioxane; water / 2 h / 20 °C
10.1: tetrahydrofuran / 3.5 h / -30 - -20 °C / Inert atmosphere
11.1: toluene-4-sulfonic acid / diethyl ether; tetrahydrofuran / 0 - 20 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / -5 - 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; sodium periodate; N-chloro-succinimide; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
toluene-4-sulfonic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;