(2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 320748-66-1
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.353
• Mol file: 320748-66-1.mol

Synonyms:(2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 3 articles about (2S,7aS)-6-oxo-2,3,5,6,7,7a-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: 93.0%

(2S,3aS,7aS)-3a-(benzoyloxy)-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-65-0) → (2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-66-1)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; for 7h; Reflux; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.08.017

Reference yield:

(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (144534-49-6) → (2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-66-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 50 h / 40 °C

2.1: 78 percent / NaHCO₃ / dimethylsulfoxide / 1 h / 90 °C

3.1: AcOH / tetrahydrofuran

3.2: 75 percent / zinc; BrCH₂CH₂Br; TMSCl / tetrahydrofuran / 9 h / 65 °C

With pyridine; dmap; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol006759x

Reference yield:

<2S-(2β,3aβ,7aβ)>-2,3,3a,6,7,7a-hexahydro-3a-benzoyloxy-6-oxo-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester (171523-63-0) → (2S,7aS)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / NaHCO₃ / dimethylsulfoxide / 1 h / 90 °C

2.1: AcOH / tetrahydrofuran

2.2: 75 percent / zinc; BrCH₂CH₂Br; TMSCl / tetrahydrofuran / 9 h / 65 °C

With sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/ol006759x

upstream raw materials:

(2S,3aS,7aS)-3a-(benzoyloxy)-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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

<2S-(2β,3aβ,7aβ)>-2,3,3a,6,7,7a-hexahydro-3a-benzoyloxy-6-oxo-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

Downstream raw materials:

(2S,3aS,7aS)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,3aS,6R,7aS)-6-hydroxy-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate

(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester