Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Phenyl chloroformate | HCID 15891 | — |
| Edukt | (4S,5R)-N-[(4-fluorophenyl)methyl]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride | HCID 68568666 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 178524305 | HCID 178524305 | 82,6% |
Reaktionsschritte
To a solution of (cis-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-(4-fluorobenzyl)amine (86) (100 mg, 0.26 mmol), triethylamine (0.091 mL, 0.656 mmol), 4-dimethylamino-pyridine (10 mg) in dichloromethane (10 mL) is added phenyl chloroformate (0.033 mL, 0.262 mmol), and the mixture is stirred at RT overnight. The reaction mixture is diluted with dichloromethane and washed with water, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is purified by chromatography on silica gel; gradient elution with heptane: EtOAc (70:30-60:40) gives 100 mg of the product 123. 1H NMR (CDCl3) δ 7.50-7.40 (m, 2H), 7.40-7.10 (m, 6H), 7.10-6.90 (m, 8H), 6.90-6.80 (m, 2H), 6.70-6.60 (m, 2H), 5.75-5.55 (m, 2H), 4.75-4.55 (m, 2H); MS: m/z 466 (M++1)
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07326792B2 |
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| Quelldatensatz | uspto-grants-2008_02 |
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| ORD ID | ord-70418bdacfd14b5cbd8f4384c80aaddf |
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| Quellennotiz | uspto-grants-2008_02 |
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