(E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

Base Information

Chemical Name:(E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid
CAS No.:1308280-26-3
Molecular Formula:C₂₄H₃₁NO₃
Molecular Weight:381.515
Hs Code.:

Synonyms:(E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

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Chemical Property of (E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

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Technology Process of (E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

There total 6 articles about (E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic 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:

Reference yield: 38.0%

: 1308280-23-0
ethyl (E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoate

: 1308280-26-3
(E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

Guidance literature:: With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1021/jm200051z

Reference yield:

: 736992-49-7
2-(1-adamantyl)-1-benzyloxy-4-bromobenzene

: 1308280-26-3
(E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 19.5 h / 111 °C

2: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C

3: toluene / 15.7 h / Reflux

4: boron tribromide / dichloromethane / -78 °C / Inert atmosphere

5: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 1.5 h / 0 °C / Inert atmosphere

With lithium hydroxide monohydrate; water; palladium diacetate; boron tribromide; diisobutylaluminium hydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 3: Wittig reaction;
DOI:10.1021/jm200051z

Reference yield:

: 1126-09-6
4-carbethoxypiperidine

: 1308280-26-3
(E)-3-{1-[3'-(1-adamantyl)-4'-hydroxyphenyl]piperidin-4-yl}-2-propenoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 19.5 h / 111 °C

2: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C

3: toluene / 15.7 h / Reflux

4: boron tribromide / dichloromethane / -78 °C / Inert atmosphere

5: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 1.5 h / 0 °C / Inert atmosphere

With lithium hydroxide monohydrate; water; palladium diacetate; boron tribromide; diisobutylaluminium hydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 3: Wittig reaction;
DOI:10.1021/jm200051z