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

Base Information

Chemical Name:(3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole
CAS No.:215609-79-3
Molecular Formula:C₂₄H₂₅NO₆S
Molecular Weight:455.532
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 15 articles about (3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-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: 98.0%

: 108-24-7
acetic anhydride

: 215609-76-0
(3R,3aS,7aS)-N-p-tolylsulfonyl-3-hydroxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole

: 215609-79-3
(3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole

Guidance literature:: With pyridine;
DOI:10.1021/jo9815249

Reference yield: 80.0%

: (3aS,7aS)-3a-(benzo[d][1,3]dioxol-5-yl)-1-tosyl-1,2,3a,6,7,7a-hexahydro-3H-indol-3-one

: 108-24-7
acetic anhydride

: 215609-79-3
(3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole

Guidance literature:: (3aS,7aS)-3a-(benzo[d][1,3]dioxol-5-yl)-1-tosyl-1,2,3a,6,7,7a-hexahydro-3H-indol-3-one; With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 - 22 ℃; for 10h;

acetic anhydride; With dmap; In pyridine; at 22 ℃; for 4h;
DOI:10.1021/acs.joc.9b00018

Reference yield:

: 40597-44-2
N-(2,2-diethoxy-ethyl)-4-methylbenzenesulfonamide

: 215609-79-3
(3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-2,3,3a,6,7,7a-hexahydroindole

Guidance literature:: Multi-step reaction with 4 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

With pyridine; 4 A molecular sieve; silica gel; iron(III) chloride; (S)-1,1'-binaphthalene-2,2'-diylbis(diphenylphosphine oxide); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; acetone;
DOI:10.1021/jo9815249