Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Thiophenacetic acid | HCID 23404 | — |
| Reactant | 7,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride | HCID 21264543 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67915819 | HCID 67915819 | 77.5% |
Reaction Steps
N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 2-(3-thienyl)acetic acid (0.99 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 15 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.24 g) and triethylamine (1.96 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred for 16 hours at 20° C., then washed with distilled water (3×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from a mixture of acetonitrile (30 cc) and isopropyl ether (40 cc). The crystals are drained, washed with isopropyl ether and dried. (3aRS,7aRS)-7,7-diphenyl-2-[2-(3-thienyl)acetyl]-4-perhydroisoindolone (2.2 g) melting at 224° C. is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05102667 |
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| Source dataset | uspto-grants-1992_04 |
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| ORD ID | ord-e7c49da93df744a392606d3171d78290 |
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| Source note | uspto-grants-1992_04 |
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