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

Base Information

• Chemical Name: 1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate
• CAS No.: 320748-68-3
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 320748-68-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate 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: 81.0%

(2S,3aS,7aS)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-67-2) → 1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate (320748-68-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃;

DOI:10.1021/ol006759x

Reference yield: 68.0%

(2S,3aS,7aS)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (320748-67-2) → (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 (320748-69-4) + 1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate (320748-68-3)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1021/ol006759x

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) → 1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate (320748-68-3)

Guidance literature:

Multi-step reaction with 5 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

4.1: 95 percent / H₂ / PtO₂ / acetic acid; ethanol / 1 h / 0 °C / 760.05 Torr

5.1: 18 percent / L-selectride / tetrahydrofuran / 3 h / -78 °C

With pyridine; dmap; hydrogen; L-Selectride; sodium hydrogencarbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; dimethyl sulfoxide;

DOI:10.1021/ol006759x

upstream 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,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

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

Downstream raw materials:

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

C₇₃H₁₂₂N₆O₁₁Si₄

C₇₃H₁₂₂N₆O₁₁Si₄

C₄₇H₇₃N₅O₉Si₂