(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:171523-58-3
Molecular Formula:C₂₆H₃₄N₂O₆
Molecular Weight:470.566
Hs Code.:

Synonyms:(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Chemical Property of (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 7 articles about (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-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:

: 171523-56-1
(2S,3aR,7aR)-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-58-3
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 34 percent / potassium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C

2: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

3: 85 percent / xylene / 8 h / Heating

4: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

With sodium tetrahydroborate; sodium periodate; cerium(III) chloride; potassium hexamethyldisilazane; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; xylene;
DOI:10.1021/ja00150a010

Reference yield:

: 144534-49-6
(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-58-3
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / DMAP, pyridine / CH₂Cl₂ / 24 h / Heating

2: 99 percent / NaBH₄, CeCl₃*7H₂O / diisopropyl ether; methanol / 2 h / 0 °C

3: 1.) tris(dibenzylideneacetone)dipalladium⁽⁰⁾*CHCl₃, tri-n-butylphosphine, HCO₂H, Et₃N, 2.) tetrapropylammonium perruthenate, N-methylmorpholine N-oxide monohydrate / 1.) THF, 60 deg C, 7 h, 2.) CH₂Cl₂, from 0 deg to RT, 4 h

4: 34 percent / potassium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C

5: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

6: 85 percent / xylene / 8 h / Heating

7: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; sodium periodate; formic acid; cerium(III) chloride; tetrapropylammonium perruthennate; potassium hexamethyldisilazane; tributylphosphine; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; di-isopropyl ether; xylene;
DOI:10.1021/ja00150a010

Reference yield:

: 171523-49-2
(2S,3aR,7S,7aS)-6-oxo-7-pent-4-enyl-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-58-3
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-oxobutyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

2: 85 percent / xylene / 8 h / Heating

3: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

With sodium tetrahydroborate; sodium periodate; cerium(III) chloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; xylene;
DOI:10.1021/ja00150a010