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

Base Information

• Chemical Name: 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid
• CAS No.: 145324-18-1
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 145324-18-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic 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: 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: 69.0%

potassium formate (590-29-4) + (E)-1-((3aR,7aS)-octahydro-2H-isoindol-2-yl)-4-phenylbut-3-en-1-one → 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid (145324-18-1)

Guidance literature:

With 1,3-dicyano-2,4,5,6-tetrakis(N,N-diphenylamino)-benzene; Methyl thiosalicylate; In dimethyl sulfoxide; for 2h; Irradiation;

DOI:10.1021/jacs.1c07562

Reference yield:

cis-hexahydroisoindoline (1470-99-1,1220913-24-5) → 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid (145324-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

2.1: sodium ethoxide / ethyl acetate / 1 h / Heating

2.2: ethyl acetate / 3 h / Heating

3.1: aq. NaOH / ethanol / 24 h

3.2: 25.4 g / ethyl acetate / 2 h / Heating

With sodium hydroxide; sodium ethanolate; triethylamine; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1080/00397910701392590

upstream raw materials:

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

ethyl 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-2-carbethoxy-butanoate

(3aR,7aS)-2-chloroacetyl-octahydro-2H-isoindole

cis-hexahydroisoindoline

Downstream raw materials:

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

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

mitiglinide