Multi-step reaction with 11 steps
1: N-Bromosuccinimide / dibenzoyl peroxide / tetrachloromethane / 18 h / Reflux
2: sodium azide / dimethyl sulfoxide / 4 h / 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 20 °C
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C
5: sodium tetrahydroborate; methanol / tetrahydrofuran / 3.33 h / 40 - 45 °C / Inert atmosphere
6: Dess-Martin periodane / dichloromethane / 2.33 h / 0 - 20 °C
7: hydroxylamine hydrochloride; sodium acetate / ethanol / 4 h / 20 °C
8: N-chloro-succinimide / N,N-dimethyl-formamide / 12 h / 20 °C
9: sodium hydrogencarbonate / 12 h / 20 °C
10: trifluoroacetic acid / dichloromethane / 20 °C
11: pyridine / N,N-dimethyl-formamide / 0.17 h / 20 °C
With
pyridine; methanol; sodium tetrahydroborate; N-chloro-succinimide; N-Bromosuccinimide; sodium azide; hydroxylamine hydrochloride; water; sodium acetate; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;