(7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

Base Information

Chemical Name:(7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide
CAS No.:1400924-80-2
Molecular Formula:C₃₁H₃₄N₂O₃
Molecular Weight:482.623
Hs Code.:

(7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

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Chemical Property of (7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

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Technology Process of (7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

There total 13 articles about (7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide 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:

: 1078-19-9
6-methoxy-3,4-dihydro-1(2H)-naphthalenone

: 1400924-79-9
(7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

: 1400924-80-2
(7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium hydride / n-heptane; dimethyl sulfoxide; tetrahydrofuran; mineral oil / 0.5 h / 20 °C

1.2: 4 h

2.1: [hydroxy(tosyloxy)iodo]benzene / water; methanol / 0 - 20 °C

3.1: pyrrolidine / toluene / 2 h / Reflux

3.2: 18 h / 100 °C

3.3: 2 h / 100 °C

4.1: ethanol; sodium / 3 h / 60 °C / Inert atmosphere; Reflux

5.1: methanesulfonic acid; DL-methionine / 48 h / 20 °C / Inert atmosphere

6.1: hydrogen / 10 wt% Pd(OH)2 on carbon / toluene / 20 h / 50 °C / 3102.97 Torr

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 20 °C

8.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere

9.1: water; lithium hydroxide / 1,4-dioxane / 50 °C

10.1: hydrogenchloride / 1,4-dioxane; water

10.2: 0.08 h / 20 °C

10.3: 48 h / 60 °C

11.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

12.1: potassium permanganate; copper(ll) sulfate pentahydrate / dichloromethane; water / 0.5 h / 20 °C

13.1: diethylamine / n-heptane; ethanol / Resolution of racemate

With pyrrolidine; hydrogenchloride; potassium permanganate; copper(ll) sulfate pentahydrate; methanesulfonic acid; ethanol; [hydroxy(tosyloxy)iodo]benzene; water; hydrogen; sodium; sodium hydride; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; DL-methionine; lithium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 10 wt% Pd(OH)2 on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; n-heptane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

: 40463-28-3
2-methoxy-5,7,8,9-tetrahydrobenzocyclohepten-6-one

: 1400924-79-9
(7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

: 1400924-80-2
(7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyrrolidine / toluene / 2 h / Reflux

1.2: 18 h / 100 °C

1.3: 2 h / 100 °C

2.1: ethanol; sodium / 3 h / 60 °C / Inert atmosphere; Reflux

3.1: methanesulfonic acid; DL-methionine / 48 h / 20 °C / Inert atmosphere

4.1: hydrogen / 10 wt% Pd(OH)2 on carbon / toluene / 20 h / 50 °C / 3102.97 Torr

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 20 °C

6.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere

7.1: water; lithium hydroxide / 1,4-dioxane / 50 °C

8.1: hydrogenchloride / 1,4-dioxane; water

8.2: 0.08 h / 20 °C

8.3: 48 h / 60 °C

9.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

10.1: potassium permanganate; copper(ll) sulfate pentahydrate / dichloromethane; water / 0.5 h / 20 °C

11.1: diethylamine / n-heptane; ethanol / Resolution of racemate

With pyrrolidine; hydrogenchloride; potassium permanganate; copper(ll) sulfate pentahydrate; methanesulfonic acid; ethanol; water; hydrogen; sodium; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; DL-methionine; lithium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 10 wt% Pd(OH)2 on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

: 13587-99-0
1-methylidene-6-methoxy-1,2,3,4-tetrahydronaphthalene

: 1400924-79-9
(7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

: 1400924-80-2
(7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-5-oxo-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide

Guidance literature:: Multi-step reaction with 12 steps

1.1: [hydroxy(tosyloxy)iodo]benzene / water; methanol / 0 - 20 °C

2.1: pyrrolidine / toluene / 2 h / Reflux

2.2: 18 h / 100 °C

2.3: 2 h / 100 °C

3.1: ethanol; sodium / 3 h / 60 °C / Inert atmosphere; Reflux

4.1: methanesulfonic acid; DL-methionine / 48 h / 20 °C / Inert atmosphere

5.1: hydrogen / 10 wt% Pd(OH)2 on carbon / toluene / 20 h / 50 °C / 3102.97 Torr

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 20 °C

7.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere

8.1: water; lithium hydroxide / 1,4-dioxane / 50 °C

9.1: hydrogenchloride / 1,4-dioxane; water

9.2: 0.08 h / 20 °C

9.3: 48 h / 60 °C

10.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

11.1: potassium permanganate; copper(ll) sulfate pentahydrate / dichloromethane; water / 0.5 h / 20 °C

12.1: diethylamine / n-heptane; ethanol / Resolution of racemate

With pyrrolidine; hydrogenchloride; potassium permanganate; copper(ll) sulfate pentahydrate; methanesulfonic acid; ethanol; [hydroxy(tosyloxy)iodo]benzene; water; hydrogen; sodium; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; DL-methionine; lithium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 10 wt% Pd(OH)2 on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; toluene;