Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Thiopheneacetic acid | HCID 15970 | — |
| Reactant | 7,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride | HCID 21264543 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67915796 | HCID 67915796 | 74% |
Reaction Steps
N,N'-Carbonyldiimidazole (0.81 g) is added to a solution of 2-(2-thienyl)acetic acid (0.71 g) in dry dichloromethane (20 cc), cooled to +5° C. The mixture is stirred for 1 hour at +5° C. and a solution of 7,7-diphenyl-4-perhydroisoindolone hydrochloride (1.6 g) and triethylamine (0.7 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred for 2 hours at +5° C. and for 16 hours at 20° C. and is 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 acetonitrile (10 cc). The crystals are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[(2-thienyl)acetyl]-4-perhydroisoindolone (1.5 g) melting at 206° 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-6279ebbe9f9f4ce2bc011ef0c9d74aac |
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| Source note | uspto-grants-1992_04 |
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