HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → 6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate | HCID 7033050 | — |
| Edukt | 6-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-one | HCID 46194050 | — |
| Lösungsmittel | Methyl Ethyl Ketone | HCID 6569 | — |
| Produkt | 6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one | HCID 59352333 | 101,7% |
Reaktionsschritte
To a stirred solution of 6-bromospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.3 g, 4.3 mmol) in 2-butanone (40.0 mL) was added cesium carbonate (4.2 g, 12.9 mmol) and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (1.4 g, 5.4 mmol). The reaction was refluxed for 16 h, filtered and concentrated in vacuo to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford 6-bromo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.75 g, 100%) as a colorless solid: MS (ES+) m/z 400.0 (M+1), 402.0 (M+1).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08263606B2 |
| Quelldatensatz | uspto-grants-2012_09 |
| ORD ID | ord-cf0b3114a8b5443f80ce562c43cc6f42 |
| Quellennotiz | uspto-grants-2012_09 |