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

HRID 553877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 553877
C(P(=O)(OCC)OCC)#N.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([CH:25]=[CH2:26])[NH:20]2)=[CH:15][CH:14]=1.[CH:27]([CH2:29][C:30](O)=[O:31])=[CH2:28].Cl>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C@H:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([CH:25]=[CH2:26])[N:20]2[C:30](=[O:31])[CH2:29][CH:27]=[CH2:28])=[CH:17][CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69069541(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidine

Produkt 1

HCID 690748621-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8471TriethylamineLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with saturated sodium bicarbonate water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d40836c90a1e41a0b06b1275bc50066d
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048878B2

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