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

HRID 553903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553903
C(P(=O)(OCC)OCC)#N.[F:11][C:12]1[CH:13]=[C:14]([C@H:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[NH:19]2)[CH:15]=[CH:16][CH:17]=1.[CH:26]([CH2:28][C:29](O)=[O:30])=[CH2:27].Cl>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:11][C:12]1[CH:13]=[C:14]([C@H:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[N:19]2[C:29](=[O:30])[CH2:28][CH:26]=[CH2:27])[CH:15]=[CH:16][CH:17]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69073751(2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidine

Produkt 1

HCID 690769341-[(2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Diethyl cyanophosphonate (1.78 mL) was added to a solution of (2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidine (748 mg), vinylacetic acid (0.96 mL), and triethylamine (3.1 mL) in DMF (15 mL) at room temperature, and the reaction solution was stirred at room temperature for 27 hours. Ethyl acetate and 1 N hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was sequentially washed with saturated sodium bicarbonate water and brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 587 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe resulting organic layer was sequentially washed with saturated sodium bicarbonate water and brine
  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-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-1c1b8e30beca4ec0a1c200602cf79875
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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