HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 67095386, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 4-(chlorocarbonyl)benzoate | HCID 81850 | — |
| 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 | Dichloromethane | HCID 6344 | — |
| Product | HCID 67095386 | HCID 67095386 | 98% |
Reaction Steps
A mixture 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 (100.0 mg, 0.23 mmol), 4-chlorocarbonyl-benzoic acid methyl ester (60.0 mg, 0.30 mmol), iPr2NEt (0.12 mL, 0.69 mmol) in CH2Cl2 (5 mL) was stirred at rt overnight. The mixture was then diluted with CH2Cl2 and washed with water, brine. The organic phase was separated, filtered and dried over Na2SO4. The mixture was then concentrated and the residue was purified by flash column (1%-15% AcOEt in Hex) to give rac-4-[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-benzoic acid methyl ester (132.0 mg, 98.0%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08017607B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-5f8dbc5537474e7ca9a86002d243a9ed |
| Source note | uspto-grants-2011_09 |