methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate

Base Information

Chemical Name:methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate
CAS No.:488862-73-3
Molecular Formula:C₁₉H₁₉NO₂
Molecular Weight:293.365
Hs Code.:

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

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

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

There total 11 articles about methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate 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: 78.0%

: 67-56-1
methanol

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

: 488862-73-3
methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate

: methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate

Guidance literature:: for 0.666667h; Irradiation;
DOI:10.1021/jo026187p

Reference yield:

: 101-82-6
2-Benzylpyridine

: 488862-73-3
methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate

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: 78 percent / 0.67 h / Irradiation

With hydrogenchloride; potassium hydroxide; n-butyllithium; 4-toluenesulfonyl azide; 18-crown-6 ether; potassium tert-butylate; hydrogen bromide; bromine; potassium diazodicarboxylate; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; 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

: 488862-73-3
methyl 6-exo-phenyl-6-endo-pyridin-2-yl-bicyclo[2.1.1]hexane-5-carboxylate

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: 78 percent / 0.67 h / Irradiation

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