Technology Process of 1-{4-[(S)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-phenyl}-piperidine-4-carboxylic acid
There total 11 articles about 1-{4-[(S)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-phenyl}-piperidine-4-carboxylic acid which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: morpholine / Reflux
2: 2-methyltetrahydrofuran / 20 °C
3: acetic acid; sulfuric acid / 15 h / 110 °C
4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide
5: n-butyllithium / tetrahydrofuran / -100 °C
6: tris-(dibenzylideneacetone)dipalladium(0); XPhos; sodium t-butanolate / toluene / 85 °C
7: lithium hydroxide; water
8: hydroxylamine hydrochloride; sodium acetate / ethanol; water / Reflux
9: hydrogenchloride
With
morpholine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); n-butyllithium; sulfuric acid; hydroxylamine hydrochloride; water; sodium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; lithium hydroxide; sodium t-butanolate; XPhos;
In
tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;
6: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmcl.2013.06.017
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 2-methyltetrahydrofuran / 20 °C
2: acetic acid; sulfuric acid / 15 h / 110 °C
3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide
4: n-butyllithium / tetrahydrofuran / -100 °C
5: tris-(dibenzylideneacetone)dipalladium(0); XPhos; sodium t-butanolate / toluene / 85 °C
6: lithium hydroxide; water
7: hydroxylamine hydrochloride; sodium acetate / ethanol; water / Reflux
8: hydrogenchloride
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); n-butyllithium; sulfuric acid; hydroxylamine hydrochloride; water; sodium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; lithium hydroxide; sodium t-butanolate; XPhos;
In
tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;
5: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmcl.2013.06.017
- Guidance literature:
-
Multi-step reaction with 7 steps
1: acetic acid; sulfuric acid / 15 h / 110 °C
2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide
3: n-butyllithium / tetrahydrofuran / -100 °C
4: tris-(dibenzylideneacetone)dipalladium(0); XPhos; sodium t-butanolate / toluene / 85 °C
5: lithium hydroxide; water
6: hydroxylamine hydrochloride; sodium acetate / ethanol; water / Reflux
7: hydrogenchloride
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); n-butyllithium; sulfuric acid; hydroxylamine hydrochloride; water; sodium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; triethylamine; lithium hydroxide; sodium t-butanolate; XPhos;
In
tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;
4: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmcl.2013.06.017
