HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → Rac-[(3r,4s)-3-(3,4-dichloro-phenyl)-4-ethylamino-pyrrolidin-1-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 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 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Rac-[(3r,4s)-3-(3,4-dichloro-phenyl)-4-ethylamino-pyrrolidin-1-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone | HCID 58009339 | 84.3% |
Reaction Steps
To a solution of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester (0.36 g, 0.66 mmol) in CH2Cl2 (10 ml) was added TFA (2 ml) at RT. Stirring was continued over night. The reaction mixture was then concentrated under vacuo, the crude dissolved in CH2Cl2, washed with aq.NaHCO3 and the organic phase was dried over Na2SO4. Purification by flash chromatography (SiO2, CH2Cl2/MeOH 95:5) yielded 0.25 g (84%) of the title compound as light yellow oil. ES-MS m/e: 449.8 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404679B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-95a0dd37449a4717b16dd2b7fda63b20 |
| Source note | uspto-grants-2013_03 |