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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 553893Generated: November 1, 2026

Hydrochloric Acid → 1-[(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

https://huagongshe.com/reaction/553893

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant3-Butenoic acidHCID 32743—
ReactantDiethyl cyanophosphonateHCID 76257—
Reactant(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidineHCID 69072776—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
SolventEthyl AcetateHCID 8857—
Product1-[(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-oneHCID 69073705—

Reaction Steps

Diethyl cyanophosphonate (0.78 mL) was added to a solution of (2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidine (422 mg), vinylacetic acid (0.44 mL), and triethylamine (1.44 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 281 mg of the title compound. The property value of the compound is as follows.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08048878B2
Source datasetuspto-grants-2011_11
ORD IDord-40f83c110b2345d3bf11d6d42540e239
Source noteuspto-grants-2011_11