HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 1-cyclopentyl-3-(beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Bromocyclopentane | HCID 8728 | — |
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 3-(beta-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazole | HCID 9801558 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 1-cyclopentyl-3-(beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole | HCID 69134386 | 58,3% |
Reaktionsschritte
To a suspension of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.050 g) and cesium carbonate (0.20 g) in N,N-dimethylformamide (1 mL) was added cyclopentyl bromide (0.055 g) at 80° C., and the mixture was stirred for 30 minutes. After cooling to room temperature, water was added to the reaction mixture, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol), and successively by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1) to give 1-cyclopentyl-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.034 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07087579B2 |
| Quelldatensatz | uspto-grants-2006_08 |
| ORD ID | ord-c3d1338347874e4b9770a415431dc81b |
| Quellennotiz | uspto-grants-2006_08 |