HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitromethane → Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitromethane | HCID 6375 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Benzyl-5-ethoxy-2-methoxycarbonyl-3,4-dihydro-2h-pyrrolium tetrafluoroborate | HCID 87177309 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate | HCID 66846370 | 18.5% |
Reaction Steps
To the mixture obtained in Example 1C (0.2 mol) in 130 mL CH2Cl2 at ambient temperature was added Et3N (33.5 mL, 0.24 mol) followed by CH3NO2 (13 mL, 0.24 mol). The mixture stirred at ambient temperature for 8 h then was diluted with CH2Cl2, the layers were separated and the organic layer was washed with 20 mL 5% H2SO4 and 20 mL brine. The organic layer was dried over anhydrous Na2SO4, concentrated and purified via column chromatography (SiO2, 50% hexanes-EtOAc) to give 10.2 g of the title compound (36.9 mmol). MS (DCl/NH3) m/z 277 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07872010B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-aabf2505b7e144e2b4f34fde01440cc3 |
| Source note | uspto-grants-2011_01 |