(3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole

Base Information

• Chemical Name: (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole
• CAS No.: 215609-83-9
• Molecular Formula: C₂₅H₂₇NO₇S
• Molecular Weight: 485.558
• Mol file: 215609-83-9.mol

Synonyms:(3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole

Chemical Property of (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole

There total 11 articles about (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole 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: 76.0%

(3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole (215609-81-7) + trimethyl orthoformate (149-73-5) → (3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole (215609-85-1) + (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole (215609-83-9)

Guidance literature:

With montmorillonite K-10; for 0.0166667h; Heating;

DOI:10.1021/jo030309b

Reference yield:

N-(2,2-diethoxy-ethyl)-4-methylbenzenesulfonamide (40597-44-2) → (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole (215609-83-9)

Guidance literature:

Multi-step reaction with 6 steps

1: (S)-BINAPO / Pd₂dba3*CHCl₃ / tetrahydrofuran / 18 h / Ambient temperature

2: 83 percent / FeCl₃*SiO₂ / acetone / Ambient temperature

3: 59 percent / 4 Angstroem molecular sieves / 230 - 240 °C

4: 98 percent / pyridine

5: 86 percent / SeO₂ / dioxane / Heating

6: 1.) Ms₂O, Et₃N / 2.) 0 deg C

With pyridine; selenium(IV) oxide; 4 A molecular sieve; silica gel; iron(III) chloride; triethylamine; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); Methanesulfonic anhydride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; acetone;

DOI:10.1021/jo9815249

Reference yield:

2-(3,4-methylenedioxyphenyl)-3-[(methoxycarbonyl)oxy]-1-cyclohexene (215609-74-8) → (3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-methoxy-2,3,3a,6,7,7a-hexahydroindole (215609-83-9)

Guidance literature:

Multi-step reaction with 6 steps

1: (S)-BINAPO / Pd₂dba3*CHCl₃ / tetrahydrofuran / 18 h / Ambient temperature

2: 83 percent / FeCl₃*SiO₂ / acetone / Ambient temperature

3: 59 percent / 4 Angstroem molecular sieves / 230 - 240 °C

4: 98 percent / pyridine

5: 86 percent / SeO₂ / dioxane / Heating

6: 1.) Ms₂O, Et₃N / 2.) 0 deg C

With pyridine; selenium(IV) oxide; 4 A molecular sieve; silica gel; iron(III) chloride; triethylamine; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); Methanesulfonic anhydride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; acetone;

DOI:10.1021/jo9815249

upstream raw materials:

methanol

(3R,3aS,6R,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole

trimethyl orthoformate

N-((S)-2-Benzo[1,3]dioxol-5-yl-cyclohex-2-enyl)-4-methyl-N-(2-oxo-ethyl)-benzenesulfonamide

Downstream raw materials:

(+)-crinamine