Multi-step reaction with 10 steps
1.1: trifluoroacetic acid; N-iodo-succinimide / 3.5 h / 20 °C
2.1: N,N,N,N,N,N-hexamethylphosphoric triamide / copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C
3.1: lithium hydroxide monohydrate / water; methanol / 0.5 h / 20 °C
3.2: pH 1
4.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / 0 °C
4.2: 1 h / -78 °C
5.1: Dess-Martin periodane / dichloromethane / 1.17 h / 0 - 20 °C
6.1: triphenylphosphine / dichloromethane / 0.08 h / 0 °C
6.2: 0.33 h / 0 °C
7.1: n-butyllithium / hexane; tetrahydrofuran / 0.42 h / -78 °C
7.2: 0.08 h / 20 °C
8.1: phosphorus tribromide / dichloromethane / 0 - 20 °C
9.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C
10.1: hydroxylamine hydrochloride; sodium acetate / methanol / 0.5 h / Reflux
With
4-methyl-morpholine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; n-butyllithium; lithium hydroxide monohydrate; hydroxylamine hydrochloride; sodium acetate; phosphorus tribromide; potassium carbonate; Dess-Martin periodane; triphenylphosphine; trifluoroacetic acid; isobutyl chloroformate;
copper(l) iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;