HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Trifluoroiodomethane | HCID 16843 | — |
| Reactant | (2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al | HCID 14674666 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol | HCID 14995339 | 24.8% |
Reaction Steps
Trifluoroiodomethane (2.3 g) was cooled to -78° C. with a trap. DMF (7 ml), (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (710 mg) and zinc (1.0 g) were added there to. And the mixture was treated with ultrasonic waves for 2 hrs. at room temperature. 1N hydrochloric acid was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (217 mg) having the following physical data:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05212191 |
| Source dataset | uspto-grants-1993_05 |
| ORD ID | ord-45d7cb3e577943959cd79a7f8d380ef0 |
| Source note | uspto-grants-1993_05 |