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

Base Information

Chemical Name:(3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole
CAS No.:677301-66-5
Molecular Formula:C₂₄H₂₅NO₇S
Molecular Weight:471.531
Hs Code.:

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

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

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

There total 18 articles about (3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-hydroxy-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: 95.0%

: 677301-64-3
(3R,3aS,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-formyloxy-2,3,3a,6,7,7a-hexahydroindole

: 677301-66-5
(3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole

Guidance literature:: With ammonium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 0.383333h;
DOI:10.1021/jo030309b

Reference yield: 71.0%

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

: 677301-66-5
(3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole

Guidance literature:: With selenium(IV) oxide; In 1,4-dioxane; for 20h; Reflux;
DOI:10.1021/acs.joc.9b00018

Reference yield:

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

: 677301-66-5
(3R,3aS,6S,7aS)-N-p-tolylsulfonyl-3-acetyloxy-3a-(3,4-methylenedioxyphenyl)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole

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.) formic acid / 1.) Mitsunobu reaction, 2.) hydrolysis

With pyridine; formic acid; selenium(IV) oxide; 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; 1,4-dioxane; acetone;
DOI:10.1021/jo9815249