HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 68379404, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Benzene, 1-bromo-3-nitro- | HCID 11457 | — |
| Reactant | (2S)-2-methylpyrrolidine | HCID 6999702 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68379404 | HCID 68379404 | 91% |
Reaction Steps
A mixture of 1-bromo-3-nitrobenzene (1.43 g, 7.06 mmol), (S)-2-methylpyrrolidine (0.5 g, 5.88 mmol), Pd2(dba)3 (0.34 g, 0.59 mmol), X-Phos (0.56 g, 1.18 mmol) and sodium carbonate (1.77 g, 16.74 mmol) in the mixture of 1,4-dioxane (20 mL) and water (20 mL) was heated to reflux for 16 hours. Then water was added, extracted with ethyl acetate and organic layer washed brine dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1) to give (S)-2-methyl-1-(3-nitrophenyl)pyrrolidine (1.1 g, 91%) as red solid. LC-MS: 207 [M+H]+, tR=1.77 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08921383B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-1aa099bf04414baeb8e5121fa2a49a4c |
| Source note | uspto-grants-2014_12 |