(3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

Base Information

Chemical Name:(3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole
CAS No.:189364-02-1
Molecular Formula:C₂₈H₃₅NO₉S
Molecular Weight:561.653
Hs Code.:

Synonyms:(3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

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Chemical Property of (3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

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Technology Process of (3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

There total 16 articles about (3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole 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: 98.0%

: 7381-30-8
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

: 189364-01-0
Carbonic acid (3R,3aS,7aS)-3a-(3,4-dimethoxy-phenyl)-6-oxo-1-(toluene-4-sulfonyl)-octahydro-indol-3-ylmethyl ester methyl ester

: 189364-02-1
(3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 6h;
DOI:10.1021/jo9701187

Reference yield:

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

: 189364-02-1
(3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

Guidance literature:: Multi-step reaction with 14 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: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

11: 91 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

12: 65 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 20 h / -10 °C

13: 79 percent / H₂ / 10percent Pd/C / CH₂Cl₂ / 3.5 h / Ambient temperature

14: 98 percent / TMSOTf / CH₂Cl₂ / 6 h / -30 °C

With pyridine; 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium naphthalenide; sodium carbonate; potassium carbonate; (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

: 189364-02-1
(3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole

Guidance literature:: Multi-step reaction with 14 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: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

11: 91 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

12: 65 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 20 h / -10 °C

13: 79 percent / H₂ / 10percent Pd/C / CH₂Cl₂ / 3.5 h / Ambient temperature

14: 98 percent / TMSOTf / CH₂Cl₂ / 6 h / -30 °C

With pyridine; 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium naphthalenide; sodium carbonate; potassium carbonate; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9701187