Multi-step reaction with 8 steps
1.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 25 °C / Reflux
2.1: thionyl chloride / 1 h / 25 °C / Reflux
3.1: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C
4.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide; sodium L-ascorbate / N,N-dimethyl-formamide / 12 h / 25 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Cooling with ice
6.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 2 h / 25 °C
7.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 0 °C
7.2: 0.75 h / Cooling with ice
8.1: hydroxylamine hydrochloride; sodium methylate / dichloromethane; methanol / -20 - 25 °C
With
N-Bromosuccinimide; copper(l) iodide; lithium aluminium tetrahydride; thionyl chloride; sodium azide; hydroxylamine hydrochloride; potassium tert-butylate; sodium methylate; sodium acetate; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate;
2,2'-azobis(isobutyronitrile);
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;