(1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate

Base Information

Chemical Name:(1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate
CAS No.:1423074-47-8
Molecular Formula:C₇H₆O₃*C₁₄H₁₈N₂
Molecular Weight:352.433
Hs Code.:

Synonyms:

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Chemical Property of (1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate

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Technology Process of (1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate

There total 19 articles about (1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate 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:

: ethyl 3-azabicyclo[3.3.1]non-7-ene-3-carboxylate

: 1423074-47-8
(1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate

Guidance literature:: Multi-step reaction with 5 steps

1: bromine / dichloromethane / 2.5 h / 10 - 20 °C

2: potassium tert-butylate / tetrahydrofuran / 5 h / 5 - 40 °C

3: sodium carbonate; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate / water; 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 25 °C

5: isopropyl alcohol; Isopropyl acetate / 0 °C / Reflux; Large scale

With 1,1'-bis-(diphenylphosphino)ferrocene; lithium aluminium tetrahydride; potassium tert-butylate; bromine; palladium diacetate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; Isopropyl acetate; water; isopropyl alcohol; 3: |Suzuki Coupling;
DOI:10.1021/op400002r

Reference yield:

: 100-50-5,61746-36-9
3-Cyclohexene-1-carboxaldehyde

: 1423074-47-8
(1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: hydroxylamine hydrochloride; sodium hydroxide / water; 2-methyltetrahydrofuran / 3.5 h / 22 - 29 °C / pH 9 / Inert atmosphere; Large scale

2.1: lithium aluminium tetrahydride / 2-methyltetrahydrofuran; tetrahydrofuran / 19.5 h / 19 - 57 °C / Large scale

3.1: sodium hydroxide / 2-methyltetrahydrofuran; tetrahydrofuran / 1 h / 2 - 5 °C / Large scale

3.2: 5 h / 0 - 5 °C / Large scale

4.1: boron trifluoride diethyl etherate / dichloromethane / 6.5 h / 25 - 26 °C / Inert atmosphere; Large scale

5.1: bromine / dichloromethane / 2.5 h / 10 - 20 °C / Large scale

6.1: potassium tert-butylate / tetrahydrofuran / 5 h / 5 - 40 °C / Large scale

7.1: sodium carbonate; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate / water; 1,4-dioxane / 3 h / 80 °C / Inert atmosphere; Large scale

8.1: hydrogenchloride / water / 30 h / 100 °C / Large scale

9.1: Supelco Chiralpak AD 20 μm columns / isopropyl alcohol; diethylamine / Resolution of racemate; Large scale

10.1: formic acid / water / 2 h / 85 - 87 °C / Large scale

11.1: isopropyl alcohol; Isopropyl acetate / 0 °C / Reflux; Large scale

With hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium aluminium tetrahydride; formic acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; potassium tert-butylate; bromine; palladium diacetate; sodium carbonate; sodium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; dichloromethane; Isopropyl acetate; water; diethylamine; isopropyl alcohol; 7.1: |Suzuki Coupling / 10.1: |Eschweiler-Clarke Methylation;
DOI:10.1021/op400002r

Reference yield:

: 1403453-42-8
(1R,5S)-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene

: 1423074-47-8
(1R,5S)-3-methyl-7-(pyridin-3-yl)-3-azabicyclo[3.3.1]non-6-ene p-hydroxybenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: formic acid / water / 2 h / 85 - 87 °C / Large scale

2: isopropyl alcohol; Isopropyl acetate / 0 °C / Reflux; Large scale

With formic acid; In Isopropyl acetate; water; isopropyl alcohol; 1: |Eschweiler-Clarke Methylation;
DOI:10.1021/op400002r