HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Ethyl trans(+/-)-2-[(2-amino-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | (1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acid | HCID 11535603 | — |
| Reactant | tert-butyl 5-amino-1,3-dihydro-2H-inden-2-carboxylate | HCID 86712355 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl trans(+/-)-2-[(2-amino-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylate | HCID 68416342 | 81% |
Reaction Steps
The same operation as in Example (93a) was performed using tert-butyl 5-amino-1,3-dihydro-2H-inden-2-carboxylate (described in Andronati, S. A.; Krys'ko, A. A.; Chugunov, B. M.; Kabanova, T. A.; Artemenko, A. G.; Russ. J. Org. Chem.; 42; 8; 2006; 1174-1182, 0.19 g, 0.77 mmol), trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid (described in Wessjohann, Ludger A.; Fulhorst, Michael; Zakharova, Svetlana; Pol. J. Chem.; 80; 4; 2006; 673-678, 182 mg, 1.15 mmol), WSC hydrochloride (0.29 g, 1.5 mmol), DMAP (10 mg) and dichloromethane (20 mL). Purification by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 2/1, 1/1, 1/2) gave 0.24 g of the title compound as a colorless solid (81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-0c8617ff5e2f460ca1b65b0dd92cc169 |
| Source note | uspto-grants-2013_09 |