6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

Base Information

Chemical Name:6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid
CAS No.:488862-65-3
Molecular Formula:C₁₈H₁₇NO₂
Molecular Weight:279.338
Hs Code.:

Synonyms:6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

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Chemical Property of 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

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Technology Process of 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

There total 11 articles about 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-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:

Reference yield: 76.0%

: 3-diazo-7-exo-phenyl-7-endo-pyridin-2-yl-bicyclo[2.2.1]heptan-2-one

: 488862-65-3
6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

: 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

Guidance literature:: With water; In 1,4-dioxane; for 2.25h; Irradiation;
DOI:10.1021/jo026187p

Reference yield:

: 101-82-6
2-Benzylpyridine

: 488862-65-3
6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C

1.2: tetrahydrofuran / 3 h / -78 °C

2.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

3.1: HBr; Br₂ / diethyl ether / 0.75 h / 20 °C

4.1: 3.7 g / t-BuOK; 18-crown-6 / tetrahydrofuran / -78 - 20 °C

5.1: 45 percent / HCl / CH₂Cl₂ / 72 h

6.1: 1.16 g / potassium azodiformate; acetic acid / methanol / 3.5 h

7.1: KOH / H₂O / 48 h

7.2: 53 percent / HCl / H₂O / 50 h / Heating

8.1: diisopropylamine; n-BuLi / tetrahydrofuran / -78 °C

8.2: 1.01 g / tetrahydrofuran / 48 h

9.1: 0.65 g / tosyl azide; triethylamine / CH₂Cl₂

10.1: 76 percent / water / dioxane / 2.25 h / Irradiation

With hydrogenchloride; potassium hydroxide; n-butyllithium; 4-toluenesulfonyl azide; 18-crown-6 ether; potassium tert-butylate; water; hydrogen bromide; bromine; potassium diazodicarboxylate; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; 5.1: Diels-Alder reaction / 7.2: Nef reaction / 10.1: Wolff rearrangement;
DOI:10.1021/jo026187p

Reference yield:

: 5-nitro-7-exo-phenyl-7-endo-(pyridin-2-yl)bicyclo[2.2.1]hept-2-ene

: 488862-65-3
6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1.16 g / potassium azodiformate; acetic acid / methanol / 3.5 h

2.1: KOH / H₂O / 48 h

2.2: 53 percent / HCl / H₂O / 50 h / Heating

3.1: diisopropylamine; n-BuLi / tetrahydrofuran / -78 °C

3.2: 1.01 g / tetrahydrofuran / 48 h

4.1: 0.65 g / tosyl azide; triethylamine / CH₂Cl₂

5.1: 76 percent / water / dioxane / 2.25 h / Irradiation

With potassium hydroxide; n-butyllithium; 4-toluenesulfonyl azide; water; potassium diazodicarboxylate; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 2.2: Nef reaction / 5.1: Wolff rearrangement;
DOI:10.1021/jo026187p