HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2405760Generated: November 1, 2026
Trifluoroacetic acid → (trans)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester
https://huagongshe.com/reaction/2405760
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine | HCID 353442 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Propenoic acid, 3-(4-chlorophenyl)-, methyl ester, (2E)- | HCID 5314314 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (trans)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester | HCID 12922292 | 255.7% |
Reaction Steps
To a solution of benzyl-methoxymethyl-trimethylsilanylmethyl-amine (2.05 mL, 8.0 mmol) and (E)-3-(4-chloro-phenyl)-acrylic acid methyl ester (1.57 g, 8.0 mmol) in dichloromethane (16 mL) was added TFA (275 mg, 2.4 mmol). The mixture was stirred at 23° C. for 30 min then treated with saturated aqueous NaHCO3 (20 mL), extracted with dichloromethane (2×50 mL), dried with MgSO4, filtered, and concentrated. Purification of the crude by flash chromatography (SiO2, hexane to 1:1 hexane:EtOAc) gave (trans)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (2.11 g, 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809326B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-0f1a08ce35f8417dbe082d0ee53cf928 |
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| Source note | uspto-grants-2014_08 |
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