(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 methyl ester

Base Information

• Chemical Name: (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 methyl ester
• CAS No.: 1400926-86-4
• Molecular Formula: C₂₆H₃₂O₃
• Molecular Weight: 392.538

Synonyms:

Chemical Property of (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 methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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 methyl ester

There total 11 articles about (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 methyl ester 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) → (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 ester (1400926-85-3) + (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 methyl ester (1400926-86-4)

Guidance literature:

Multi-step reaction with 11 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: sodium hydride / dimethyl sulfoxide; tetrahydrofuran; mineral oil / 0.17 h / -10 °C

8.2: 1.45 h / -10 - 20 °C

9.1: copper(l) iodide / diethyl ether; tetrahydrofuran / -40 - 0 °C / Inert atmosphere

9.2: 18.08 h

10.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 22 h / 90 °C

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

With pyrrolidine; methanesulfonic acid; ethanol; [hydroxy(tosyloxy)iodo]benzene; hydrogen; sodium; sodium hydride; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; DL-methionine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; 10 wt% Pd(OH)2 on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 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) → (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 ester (1400926-85-3) + (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 methyl ester (1400926-86-4)

Guidance literature:

Multi-step reaction with 9 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: sodium hydride / dimethyl sulfoxide; tetrahydrofuran; mineral oil / 0.17 h / -10 °C

6.2: 1.45 h / -10 - 20 °C

7.1: copper(l) iodide / diethyl ether; tetrahydrofuran / -40 - 0 °C / Inert atmosphere

7.2: 18.08 h

8.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 22 h / 90 °C

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

With pyrrolidine; methanesulfonic acid; ethanol; hydrogen; sodium; sodium hydride; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; DL-methionine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; 10 wt% Pd(OH)2 on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; diethyl ether; ethanol; n-heptane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

1-methylidene-6-methoxy-1,2,3,4-tetrahydronaphthalene (13587-99-0) → (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 methyl ester (1400926-85-3) + (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 methyl ester (1400926-86-4)

Guidance literature:

Multi-step reaction with 10 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: sodium hydride / dimethyl sulfoxide; tetrahydrofuran; mineral oil / 0.17 h / -10 °C

7.2: 1.45 h / -10 - 20 °C

8.1: copper(l) iodide / diethyl ether; tetrahydrofuran / -40 - 0 °C / Inert atmosphere

8.2: 18.08 h

9.1: triethylamine / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 22 h / 90 °C

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

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

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

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