(3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester
CAS No.:1027080-11-0
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:(3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

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Chemical Property of (3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

There total 13 articles about (3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-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:

: 109380-07-6,109431-74-5,122797-27-7,61426-49-1
2-bromocyclohex-2-en-1-ol

: 1027080-11-0
(3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) 2M Na₂CO₃, Pd(PPh₃)4, 2.) H₂O₂ / 1.) benzene, EtOH, 80 deg C, 1.3 h, 2.) room temperature, 1 h.

2: 99 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: (S)-BINAPO, Pd₂dba3*CHCl₃ / tetrahydrofuran / 19 h / Ambient temperature

4: 71 percent / sodium naphthalenide / tetrahydrofuran / 0.83 h / -78 °C

5: 45 percent / K₂CO₃ / various solvent(s) / 216 h / 90 °C

7: 85 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

8: H₂ / 10percent Pd/C / methanol / 9 h / Ambient temperature

9: pyridine / CH₂Cl₂ / 12 h / Ambient temperature

10: H₂ / 10percent Pd/C / methanol / 10 h / Ambient temperature

11: 80 percent / Dess-Martin reagent / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) room temperature, 1 h.

12: 62 percent / RhCl(PPh₃)3 / various solvent(s) / 24 h / Heating

13: 1.) sodium naphthalenide, 2.) K₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) CH₂Cl₂, room temperature, 19 h.

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; RhCl(PPh₃)3; hydrogen; dihydrogen peroxide; sodium naphthalenide; sodium carbonate; potassium carbonate; Dess-Martin periodane; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9701187

Reference yield:

: 122775-35-3
3,4-Dimethoxyphenylboronic acid

: 1027080-11-0
(3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) 2M Na₂CO₃, Pd(PPh₃)4, 2.) H₂O₂ / 1.) benzene, EtOH, 80 deg C, 1.3 h, 2.) room temperature, 1 h.

2: 99 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: (S)-BINAPO, Pd₂dba3*CHCl₃ / tetrahydrofuran / 19 h / Ambient temperature

4: 71 percent / sodium naphthalenide / tetrahydrofuran / 0.83 h / -78 °C

5: 45 percent / K₂CO₃ / various solvent(s) / 216 h / 90 °C

7: 85 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

8: H₂ / 10percent Pd/C / methanol / 9 h / Ambient temperature

9: pyridine / CH₂Cl₂ / 12 h / Ambient temperature

10: H₂ / 10percent Pd/C / methanol / 10 h / Ambient temperature

11: 80 percent / Dess-Martin reagent / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) room temperature, 1 h.

12: 62 percent / RhCl(PPh₃)3 / various solvent(s) / 24 h / Heating

13: 1.) sodium naphthalenide, 2.) K₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) CH₂Cl₂, room temperature, 19 h.

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; RhCl(PPh₃)3; hydrogen; dihydrogen peroxide; sodium naphthalenide; sodium carbonate; potassium carbonate; Dess-Martin periodane; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9701187

Reference yield:

: 189363-85-7
2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ol

: 1027080-11-0
(3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-octahydro-indole-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 99 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: (S)-BINAPO, Pd₂dba3*CHCl₃ / tetrahydrofuran / 19 h / Ambient temperature

3: 71 percent / sodium naphthalenide / tetrahydrofuran / 0.83 h / -78 °C

4: 45 percent / K₂CO₃ / various solvent(s) / 216 h / 90 °C

6: 85 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

7: H₂ / 10percent Pd/C / methanol / 9 h / Ambient temperature

8: pyridine / CH₂Cl₂ / 12 h / Ambient temperature

9: H₂ / 10percent Pd/C / methanol / 10 h / Ambient temperature

10: 80 percent / Dess-Martin reagent / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) room temperature, 1 h.

11: 62 percent / RhCl(PPh₃)3 / various solvent(s) / 24 h / Heating

12: 1.) sodium naphthalenide, 2.) K₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) CH₂Cl₂, room temperature, 19 h.

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; RhCl(PPh₃)3; hydrogen; sodium naphthalenide; potassium carbonate; Dess-Martin periodane; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9701187