Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile | HCID 67095372 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 51356118 | HCID 51356118 | 44.2% |
Reaction Steps
To a solution of rac (2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (42.1 mg, 0.10 mmol) in DMF (3 mL) was added potassium carbonate (43.3 mg, 0.313 mmol) and the reaction mixture was stirred at rt under argon for 21 hrs. The reaction mixture was diluted with ethyl acetate and washed with water (2×) and brine. The organic phase was separated, filtered and dried over Na2SO4. The mixture was then concentrated and purified by flash chromatography to give rac [(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid ethyl ester (22.3 mg, 44.2%,) as a white amorphous solid. HRMS (ES+) m/z Calcd for C26H28Cl2F2N2O2+H [(M+H)+]: 509.1569; Found: 509.1569.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08017607B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-760740d639844d89b50f499abc883aa5 |
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| Source note | uspto-grants-2011_09 |
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