(7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-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: (7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-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.: 1400924-69-7
• Molecular Formula: C₃₁H₃₆N₂O₂
• Molecular Weight: 468.639

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

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

Chemical Property:

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Technology Process of (7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-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 12 articles about (7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-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:

6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → (7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide (1400924-70-0) + (7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide (1400924-69-7)

Guidance literature:

Multi-step reaction with 12 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: diethylamine / n-heptane; ethanol / Resolution of racemate

With pyrrolidine; hydrogenchloride; 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:

2-methoxy-5,7,8,9-tetrahydrobenzocyclohepten-6-one (40463-28-3) → (7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide (1400924-70-0) + (7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide (1400924-69-7)

Guidance literature:

Multi-step reaction with 10 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: diethylamine / n-heptane; ethanol / Resolution of racemate

With pyrrolidine; hydrogenchloride; 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:

1-methylidene-6-methoxy-1,2,3,4-tetrahydronaphthalene (13587-99-0) → (7aR,9S,11aR)-11a-benzyl-9-ethyl-9-hydroxy-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide (1400924-70-0) + (7aS,9R,11aS)-11a-benzyl-9-ethyl-9-hydroxy-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[a,c]cycloheptene-3-carboxylic acid (2-methyl-pyridin-3-yl)-amide (1400924-69-7)

Guidance literature:

Multi-step reaction with 11 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: diethylamine / n-heptane; ethanol / Resolution of racemate

With pyrrolidine; hydrogenchloride; 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;

upstream raw materials:

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

2-methoxy-5,7,8,9-tetrahydrobenzocyclohepten-6-one

1-methylidene-6-methoxy-1,2,3,4-tetrahydronaphthalene

(4aR,11bS)-11b-benzyl-9-hydroxy-1,2,4,4a,5,6,7,11b-octahydro-dibenzo[a,c]cyclohepten-3-one; compound with (4aS,11bR)-11b-benzyl-9-hydroxy-1,2,4,4a,5,6,7,11b-octahydro-dibenzo[a,c]cyclohepten-3-one

Downstream raw materials:

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

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