HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → rac-[(3S,4R)-4-(3 4-Dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Rac-[(3s,4r)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester | HCID 67025594 | — |
| Reactant | 1-Piperazinecarbonyl chloride, 4-(methylsulfonyl)- | HCID 79886470 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | rac-[(3S,4R)-4-(3 4-Dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester | HCID 67026416 | 97.6% |
Reaction Steps
To a solution of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester (0.25 g, 0.69 mmol) in CH2Cl2 (5 ml) was added ethyl-diisopropyl-amine (0.20 ml, 1.1 mmol) and 4-methanesulfonyl-piperazine-1-carbonyl chloride (189 mg, 0.83 mmol). Stirring was continued over night at RT, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc) afforded 0.37 g (97%) of the title compound as a white solid. ES-MS m/e: 549.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404679B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-24793f48807642adb391763dbdefd298 |
| Source note | uspto-grants-2013_03 |