HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1478604Generated: October 31, 2026
Sodium Iodide → (S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate
https://huagongshe.com/reaction/1478604
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | tert-Butyl (3S)-3-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}piperidine-1-carboxylate | HCID 45158786 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate | HCID 10083012 | 93.3% |
Reaction Steps
(S)-tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate (8.85 g, 24 mmol) was dissolved in DMF (100 ml), and then NaN3 (6.24 g, 96 mmol) and NaI (0.36 g, 2.40 mmol) were added, followed by stirring at 70° C. for 4 hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:10), to give (S)-tert-butyl 3-(azidomethyl)piperidine-1-carboxylate (5.38 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09403831B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-6fca49b2a8844c7dbe2762b1fbb66294 |
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| Source note | uspto-grants-2016_08 |
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