Technology Process of 1-[(2-fluoro-4-{2-[(1S,2R)-2-{1-(5-isopropyl-1,2,4-oxadiazol-3-yl)piperidin-4-yl}cyclopropyl]ethoxy}phenyl)acetyl]azetidin-3-ol
There total 12 articles about 1-[(2-fluoro-4-{2-[(1S,2R)-2-{1-(5-isopropyl-1,2,4-oxadiazol-3-yl)piperidin-4-yl}cyclopropyl]ethoxy}phenyl)acetyl]azetidin-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: sulfuric acid
2.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 20 °C / Inert atmosphere
3.1: sodium hydroxide / methanol / 1 h / 20 °C
3.2: pH 5
4.1: benzotriazol-1-ol; (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride / dichloromethane / 0.08 h / 20 °C
4.2: 20 °C
With
di-isopropyl azodicarboxylate; (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride; benzotriazol-1-ol; triphenylphosphine; sodium hydroxide;
sulfuric acid;
In
methanol; dichloromethane;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C
1.2: 1 h / -78 °C
2.1: hydrogen; quinoline / Lindlars catalyst / ethyl acetate / 0.67 h
3.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere
3.2: 0.17 h
3.3: 24 h / 0 °C
4.1: hydrogen / palladium(II) hydroxide / ethyl acetate; ethanol / 2585.81 Torr
4.2: 0 °C
4.3: 0.5 h / 20 °C
5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
6.1: sodium hydrogencarbonate / dichloromethane; water / 0.08 h / 0 °C
6.2: 1.5 h / 0 - 20 °C
7.1: hydroxylamine / ethanol; water / 1 h / 65 °C
8.1: pyridine / 3 h / 80 °C
8.2: 4 h / 50 °C
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 20 °C / Inert atmosphere
10.1: sodium hydroxide / methanol / 1 h / 20 °C
10.2: pH 5
11.1: benzotriazol-1-ol; (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride / dichloromethane / 0.08 h / 20 °C
11.2: 20 °C
With
pyridine; quinoline; hydrogenchloride; n-butyllithium; di-isopropyl azodicarboxylate; (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride; hydrogen; hydroxylamine; diethylzinc; sodium hydrogencarbonate; benzotriazol-1-ol; triphenylphosphine; sodium hydroxide;
palladium(II) hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: hydrogen; quinoline / Lindlars catalyst / ethyl acetate / 0.67 h
2.1: diethylzinc / dichloromethane; diethyl ether / 0.17 h / -20 °C / Inert atmosphere
2.2: 0.17 h
2.3: 24 h / 0 °C
3.1: hydrogen / palladium(II) hydroxide / ethyl acetate; ethanol / 2585.81 Torr
3.2: 0 °C
3.3: 0.5 h / 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
5.1: sodium hydrogencarbonate / dichloromethane; water / 0.08 h / 0 °C
5.2: 1.5 h / 0 - 20 °C
6.1: hydroxylamine / ethanol; water / 1 h / 65 °C
7.1: pyridine / 3 h / 80 °C
7.2: 4 h / 50 °C
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 20 °C / Inert atmosphere
9.1: sodium hydroxide / methanol / 1 h / 20 °C
9.2: pH 5
10.1: benzotriazol-1-ol; (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride / dichloromethane / 0.08 h / 20 °C
10.2: 20 °C
With
pyridine; quinoline; hydrogenchloride; di-isopropyl azodicarboxylate; (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride; hydrogen; hydroxylamine; diethylzinc; sodium hydrogencarbonate; benzotriazol-1-ol; triphenylphosphine; sodium hydroxide;
palladium(II) hydroxide;
In
1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;