HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (S)-[1-(2-Benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine | HCID 1514396 | — |
| Reactant | 2-Benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione | HCID 22624009 | — |
| Solvent | Chloroform methanol | HCID 21584188 | — |
| Product | (S)-[1-(2-Benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester | HCID 86756246 | 63.9% |
Reaction Steps
Following the procedure of Example B2, 2-benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione (0.20 g, 0.55 mmol, from Example A2), (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (0.11 g, 0.60 mmol), triethyl amine (0.11 g, 1.1 mmol) were reacted at ambient temperature for 5 hours. Column chromatography of the crude product on silica using chloroform/methanol (20:1) gave 0.18 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06362181B1 |
| Source dataset | uspto-grants-2002_03 |
| ORD ID | ord-b969afdf602d4e368b9674d9013498cc |
| Source note | uspto-grants-2002_03 |