HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 559288Generated: October 29, 2026
Trifluoroacetic acid → 4-((3SR,4RS)-4-Acetyl-1-benzyl-pyrrolidin-3-yl)-benzonitrile
https://huagongshe.com/reaction/559288
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine | HCID 353442 | — |
| Reactant | 4-[(1E)-3-Oxo-1-buten-1-yl]benzonitrile | HCID 11126721 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-((3SR,4RS)-4-Acetyl-1-benzyl-pyrrolidin-3-yl)-benzonitrile | HCID 66999181 | 33% |
Reaction Steps
A solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (22.46 g, 94.6 mmol) in CH2Cl2 (100 mL) was added dropwise, over a 30 minutes period, to a stirred solution of 4-((E)-3-oxo-but-1-enyl)-benzonitrile (10.8 g, 63.1 mmol) and trifluoroacetic acid (0.48 mL, 6.30 mmol) in CH2Cl2 (40 mL) at 0° C. The ice bath was removed, and the solution was stirred at 25° C. for an additional 48 h. It was then concentrated and purification by flash chromatography (SiO2, EtOac/Heptane 1:1) afforded 6.3 g (33%) of the title compound as a yellow oil. ES-MS m/e: 305.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08063075B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-40b481b169e94a9c823c1bf64d8c6c80 |
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| Source note | uspto-grants-2011_11 |
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