Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 1,10-Phenanthroline | HCID 1318 | — |
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | tert-Butyl (2R)-2-{[(2-bromophenyl)amino]carbonyl}pyrrolidine-1-carboxylate | HCID 68338101 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | 1,2-Dimethoxyethane | HCID 8071 | — |
| Produkt | HCID 68338089 | HCID 68338089 | 58% |
Reaktionsschritte
In a 25 mL flask, tert-butyl (2R)-2-{[(2-bromophenyl)amino]carbonyl}pyrrolidine-1-carboxylate (194 mg, 0.53 mmol; which may be prepared as described in Step 1) was dissolved in DME (4 mL) under nitrogen at room temperature. CuI (6 mg, 0.03 mmol), Cs2CO3(261 mg, 0.80 mmol) and 1,10-phenanthroline (26 mg, 0.14 mmol) were added then the reaction mixture was heated at 85° C. for 24 h. The mixture was cooled to room temperature and concentrated to dryness. The residue was dissolved in dichloromethane and filtered on Celite to eliminate the cupper residue. The filtrate was concentrated and the residue purified on preparative TLC (Pentane/EtOAc, 85/15 to 50/50) to give the title compound (88 mg, 58%) as a solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09051321B2 |
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| Quelldatensatz | uspto-grants-2015_06 |
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| ORD ID | ord-a2be8fb37944461cb5ee74dbbaeb8db7 |
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| Quellennotiz | uspto-grants-2015_06 |
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