HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1484083Generated: October 26, 2026
p-Octylbenzoic acid → (S)-1-(4-octylbenzoyl)pyrrolidine-2-carbonitrile
https://huagongshe.com/reaction/1484083
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | p-Octylbenzoic acid | HCID 19147 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate | HCID 6951263 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-1-(4-octylbenzoyl)pyrrolidine-2-carbonitrile | HCID 66927397 | 40% |
Reaction Steps
General procedure D was used to deprotect 0.4 grams (2.05 mmols) of 28 in 21 mL of dichloromethane and trifluoroacetic acid. After work-up, the TFA salt of 28 was then coupled to 0.6 grams (2.05 mmols) of 4-octylbenzoic acid with 1.1 grams (2.05 mmols) of PyBOP and 1.1 grams (8.2 mmols) of N,N-diisopropylethylamine in 21 mL of dichloromethane according to general procedure E and heating at 50° C. After previously described work-up and purification procedures (column chromatography, 25% EtOAc in hexanes) 0.256 grams (0.82 mmols, 40%) of the title product was recovered.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09421177B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1ab72fbfd33a4e6d8b70fd0664be6d3b |
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| Source note | uspto-grants-2016_08 |
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