HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Carbonate → 2-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methylbenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Carbonate | HCID 11125 | — |
| Reactant | 2-Chloro-4-fluoro-3-methylbenzonitrile | HCID 44550971 | — |
| Reactant | (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine | HCID 55299039 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 2-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methylbenzonitrile | HCID 15940254 | 16.3% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of compound 1 (1.56 g), 2-chloro-4-fluoro-3-methylbenzonitrile (1.27 g), lithium carbonate (1.16 g) and DMSO (37.5 ml) was stirred at 100° C. for 1 hr. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was washed with water, dried (sodium sulfate), and concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), and crystallized from ethyl acetate-hexane to give the title compound (357 mg) as crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08592452B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-03846190ece646a489999390347edb5b |
| Source note | uspto-grants-2013_11 |