(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-aminophenyl)-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-aminophenyl)-amide
CAS No.:1400925-84-9
Molecular Formula:C₃₁H₃₆N₂O₂
Molecular Weight:468.639
Hs Code.:

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-aminophenyl)-amide

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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-aminophenyl)-amide

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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-aminophenyl)-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-aminophenyl)-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: 25.0%

: 1400926-85-3
(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

: 95-54-5
1,2-diamino-benzene

: 1400925-85-0
(3R,4aS,11bS)-9-(1H-benzoimidazol-2-yl)-11b-benzyl-3-ethyl-2,3,4,4a,5,6,7,11b-octahydro-1H-dibenzo[a,c]cyclohepten-3-ol

: 1400925-84-9
(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 (2-aminophenyl)-amide

Guidance literature:: 1,2-diamino-benzene; With trimethylaluminum; In toluene; at 20 ℃; for 0.25h;

(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; In toluene; at 100 ℃; for 72h;

Reference yield:

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

: 1400925-85-0
(3R,4aS,11bS)-9-(1H-benzoimidazol-2-yl)-11b-benzyl-3-ethyl-2,3,4,4a,5,6,7,11b-octahydro-1H-dibenzo[a,c]cyclohepten-3-ol

: 1400925-84-9
(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 (2-aminophenyl)-amide

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: 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

12.1: trimethylaluminum / toluene / 0.25 h / 20 °C

12.2: 72 h / 100 °C

With pyrrolidine; methanesulfonic acid; ethanol; [hydroxy(tosyloxy)iodo]benzene; hydrogen; trimethylaluminum; 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:

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

: 1400925-85-0
(3R,4aS,11bS)-9-(1H-benzoimidazol-2-yl)-11b-benzyl-3-ethyl-2,3,4,4a,5,6,7,11b-octahydro-1H-dibenzo[a,c]cyclohepten-3-ol

: 1400925-84-9
(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 (2-aminophenyl)-amide

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: 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

10.1: trimethylaluminum / toluene / 0.25 h / 20 °C

10.2: 72 h / 100 °C

With pyrrolidine; methanesulfonic acid; ethanol; hydrogen; trimethylaluminum; 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;