HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 1-Benzyl-3-(3,5-dichloro-2-fluoro-phenyl)-3-(trifluoromethyl)pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine | HCID 353442 | — |
| Reactant | 1,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene | HCID 87159014 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Benzyl-3-(3,5-dichloro-2-fluoro-phenyl)-3-(trifluoromethyl)pyrrolidine | HCID 87158515 | 47.7% |
Reaction Steps
1,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene (6.2 g) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (4.7 g) were dissolved in dichloromethane (100 ml) and slowly added dropwise with a dichloromethane solution (8 ml) of anhydrous trifluoroacetic acid (0.15 ml) under ice cooling. Upon the completion of the dropwise addition, the reaction temperature was raised to room temperature and stirred overnight. The reaction solution was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain 1-benzyl-3-(3,5-dichloro-2-fluorophenyl)-3-(trifluoromethyl)pyrrolidine (3.7 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09206122B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-2377215399684a16b24c1c595f2cadc3 |
| Source note | uspto-grants-2015_12 |