Hydrochloric Acid → methyl (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate

HRID 1436121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436121
Cl.C(OC([NH:9][C@H:10]([CH2:15][CH2:16][CH2:17][C:18](=O)[C:19]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=1)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C>C(OCC)(=O)C>[F:27][C:21]1[CH:20]=[C:19]([C@H:18]2[NH:9][C@@H:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][CH2:17]2)[CH:24]=[C:23]([F:25])[C:22]=1[F:26]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 69005362methyl(R)-2-tert-butoxycarbonylamino-6-oxo-6-(3,4,5-trifluorophenyl)hexanoate

Produkt 1

HCID 67372196methyl (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylateAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A solution of 4 N hydrochloric acid in ethyl acetate (20 mL) was added to a solution of methyl(R)-2-tert-butoxycarbonylamino-6-oxo-6-(3,4,5-trifluorophenyl)hexanoate (4.0 g) in ethyl acetate (20 mL), and the reaction solution was stirred at room temperature for 14 hours. The reaction solution was concentrated under reduced pressure. Then, ethyl acetate and saturated sodium bicarbonate water were added to the residue, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. 10% palladium-carbon (100 mg) was added to a solution of the resulting residue in ethyl acetate (50 mL), and the reaction solution was stirred in a hydrogen stream at room temperature for six hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 2.7 g of the title compound. The property value of the compound is as follows.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThen, ethyl acetate and saturated sodium bicarbonate water were added to the residue
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. addition10% palladium-carbon (100 mg) was added to a solution of the resulting residue in ethyl acetate (50 mL)
  7. stirringthe reaction solution was stirred in a hydrogen stream at room temperature for six hours
  8. filtrationThe reaction solution was filtered through celite
  9. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd36cbde94524b7fb5e98f33447021a6
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618960B2

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