Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Chlorophenylacetic acid | HCID 15879 | — |
| Reactant | 7,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride | HCID 21264543 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67916035 | HCID 67916035 | 71.3% |
Reaction Steps
N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 3-chlorophenylacetic acid (1.19 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 (2.28 g) and triethylamine (1.96 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred at 20° C. for 16 hours, then washed with water (2×150 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The meringue obtained is crystallized from a mixture of acetonitrile (30 cc) and isopropyl ether (100 cc). The crystals are drained, washed with isopropyl ether and dried. (3aRS,7aRS)-7,7-diphenyl-2-[(3-chlorophenyl)acetyl]-4-perhydroisoindolone (2.2 g) is obtained in the form of white crystals melting at 179° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05102667 |
|---|
| Source dataset | uspto-grants-1992_04 |
|---|
| ORD ID | ord-0814b3f5832c417ba2981db85664a67a |
|---|
| Source note | uspto-grants-1992_04 |
|---|