Multi-step reaction with 10 steps
1.1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
3.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 - 20 °C
3.2: 0.33 h / 0 °C
4.1: 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; 1,2-dimethoxyethane / 4 h / 0 - 20 °C
5.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
5.2: 1 h / -78 - 0 °C / Inert atmosphere
6.1: pyridinium hydrobromide perbromide / N,N-dimethyl-formamide / 0.83 h / 20 °C / Inert atmosphere
7.1: N,N-dimethyl-formamide; ethanol / 2 h / 60 °C / Inert atmosphere
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 5 h / 20 °C
9.1: bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
10.1: trifluoroacetic acid / water / 5 h
With
4-methyl-morpholine; pyridine; dmap; isopropylmagnesium chloride; pyridinium hydrobromide perbromide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
3.1: |Grignard Reaction / 3.2: |Grignard Reaction;
DOI:10.1002/cmdc.201402424