HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1993656Generated: October 31, 2026
Triphenylphosphine → 4-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/1993656
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | Tert-butyl 4-hydroxypiperidine-1-carboxylate | HCID 643502 | — |
| Reactant | HCID 178433443 | HCID 178433443 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester | HCID 68535302 | 80% |
Reaction Steps
Add diisopropyl azodicarboxylate (3.0 mL, 15.5 mmol) dropwise to a cold mixture of 6-methyl-5-nitro-pyridin-2-ol (1.54 g, 10.0 mmol), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.05 g, 10.0 mmol), and triphenylphosphine (4.02 g, 15.3 mmol) in THF (25 mL) at 0° C. After addition is complete, remove cooling bath and stir the reaction mixture at 22° C. overnight. Concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to provide 4-(6-Methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil (2.69 g, 80% yield). MS(ES): m/z=338.2 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07652015B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-8e6c4b8f165247ad9427c068060f673a |
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| Source note | uspto-grants-2010_01 |
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