Hydrochloric Acid → 2,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester

HRID 1804760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804760
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]([CH3:21])[CH2:9]1)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[CH3:21][CH:10]1[CH:11]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13][NH:8][CH2:9]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 668417832,2-Dimethyl-propionic acid (3RS,4RS)-1-benzyl-3-methyl-piperidin-4-yl ester

Produkt 1

HCID 668421342,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Palladium hydroxide (20% on carbon, 1.5 g) is placed in a round-bottom flask under an argon atmosphere and covered with methanol, A solution of 2,2-dimethyl-propionic acid (3RS,4RS)-1-benzyl-3-methyl-piperidin-4-yl ester (4) (15 g, 51.8 mmol) in 300 ml of methanol is added, followed by an 1.3M methanolic HCl solution (62 ml, 78 mmol). Then the mixture is hydrogenated under normal pressure for 20 h. The solution is filtrated through celite and evaporated under reduced pressure. The residue is dissolved in diethyl ether and washed with 1N aqueous sodium hydroxide solution and brine. The combined organic layers are dried over Na2SO4 and evaporated under reduced pressure.

Aufarbeitung

  1. filtrationThe solution is filtrated through celite
  2. customevaporated under reduced pressure
  3. dissolutionThe residue is dissolved in diethyl ether
  4. washwashed with 1N aqueous sodium hydroxide solution and brine
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dfe6ecf1565c49deb091fc4df364aa91
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354431B2

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