HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 6-{(SR)-1-[(3RS,4SR)-1-(4-Cyano-piperidine-1-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Cyanopiperidine | HCID 138223 | — |
| Reactant | (3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride | HCID 86628181 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-{(SR)-1-[(3RS,4SR)-1-(4-Cyano-piperidine-1-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile | HCID 67327691 | 69% |
Reaction Steps
To a stirred solution of (3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride (30 mg, 0.070 mmol) in CH2Cl2 (4 mL) were added Et3N (0.015 mL, 0.11 mmol) and piperidine-4-carbonitrile (commercially available) (9 mg, 0.084 mmol). Stirring was continued overnight, and the reaction mixture was concentrated under vacuo and directly purified by flash chromatography (SiO2, EtOAc) to yield 24 mg (69%) the title compound as light yellow oil. ES-MS m/e: 498.0 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07812021B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-105de65fd74d44909e7ed76bd1bb57de |
| Source note | uspto-grants-2010_10 |