4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid

Base Information

• Chemical Name: 4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid
• CAS No.: 145323-82-6
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• Mol file: 145323-82-6.mol

Synonyms:4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid

Chemical Property of 4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid

There total 1 articles about 4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid 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: 74.9%

cis-hexahydroisoindoline (1470-99-1,1220913-24-5) + (E)-benzylidenesuccinic anhydride (125702-11-6) → 4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid (145323-82-6)

Guidance literature:

In dichloromethane; a) 0 deg C, 2 h, b) RT, overnight;

DOI:10.1248/cpb.45.1518

Reference yield: 90.6%

4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid (145323-82-6) → 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid (145324-18-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr;

DOI:10.1248/cpb.45.1518

Reference yield:

4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid (145323-82-6) → mitiglinide (145375-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90.6 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr

2: 39.1 percent / DCC, DMAP / CH₂Cl₂ / a) 0 deg C, 2 h, b) RT, overnight

3: 71.5 percent / 2 N NaOH / methanol / Ambient temperature

With dmap; sodium hydroxide; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1248/cpb.45.1518

upstream raw materials:

cis-hexahydroisoindoline

(E)-benzylidenesuccinic anhydride

Downstream raw materials:

4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid

mitiglinide

(S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid (S)-benzylcarbamoyl-phenyl-methyl ester