HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Rac-[(3s,4r)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | rel-tert-Butyl ((3S,4R)-4-(4-chlorophenyl)pyrrolidin-3-yl)(methyl)carbamate | HCID 67025587 | — |
| Reactant | 1-Piperazinecarbonyl chloride, 4-(methylsulfonyl)- | HCID 79886470 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Rac-[(3s,4r)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester | HCID 67026258 | 75.8% |
Reaction Steps
To a solution of rac-[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (0.76 g, 2.46 mmol) in CH2Cl2 (10 ml) was added ethyl-diisopropyl-amine (0.51 ml, 2.95 mmol) and 4-methanesulfonyl-piperazine-1-carbonyl chloride (0.61 g, 2.7 mmol). Stirring was continued over night at RT, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/Hx 1:1) afforded 0.87 g (70%) of the title compound as a white solid. ES-MS m/e: 501.4 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404679B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-19362d6ef2524c64816428803127f8bd |
| Source note | uspto-grants-2013_03 |