HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-Butenoic acid | HCID 32743 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | (2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidine | HCID 69069541 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one | HCID 69074862 | — |
Reaction Steps
Diethyl cyanophosphonate (0.67 mL) was added to a solution of (2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidine (320 mg), vinylacetic acid (0.37 mL), and triethylamine (1.23 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for nine hours. 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 100 mg of the title compound. The property value of the compound is as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08048878B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-d40836c90a1e41a0b06b1275bc50066d |
| Source note | uspto-grants-2011_11 |