Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Carbonate | HCID 11125 | — |
| Reactant | 2-Chloro-3,4-difluorobenzonitrile | HCID 21691052 | — |
| Reactant | (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine | HCID 55299039 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59370514 | HCID 59370514 | 64.1% |
Reaction Steps
A mixture of (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine 1/2 oxalate (639 mg), 2-chloro-3,4-difluorobenzonitrile (491 mg), lithium carbonate (669 mg) and dimethyl sulfoxide (13 mL) was stirred at 90° C. for 1 hr. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-hexane). The obtained solid was recrystallized from ethyl acetate to give the title compound as crystals (yield: 538 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592452B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-f3a7431aafa746d48bc2aa22635d78ff |
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| Source note | uspto-grants-2013_11 |
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