Hydrochloric Acid → HCID 19439052, Verbindung

HRID 1920751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920751
[OH-].[Na+].C([O:5][C:6](=[O:18])[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9]1)C.Cl>O.C(O)C>[C:14]([N:11]1[CH2:10][CH2:9][CH:8]([CH2:7][C:6]([OH:18])=[O:5])[CH2:13][CH2:12]1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57733330HCID 57733330, Verbindung

Produkt 1

HCID 19439052HCID 19439052, VerbindungAusbeute 19,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

To a solution of NaOH in water/ethanol (v/v=40/10, 50 mL) (1-tert-butyl-piperidin-4-yl)-acetic acid ethyl ester (4.03 g, 17.8 mmol) was added and the mixture was stirred at r.t. overnight. 1 N aq. HCl was added to adjust the pH to 5. Volotiles were evaporated in vacuo, the residue was diluted with methanol (30 mL), and the insoluble inorganic salts were removed by filtration. The filtrate was concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH=20/1 to 5/1) to give 0.7 g of title compound as a light grey powder. 1H NMR (400 MHz, DMSO-d6): 3.15-3.08 (br m, 2H), 2.30 (br t, J=11.2 Hz, 2H), 2.05 (d, J=6.4 Hz, 2H), 1.71-1.68 (m, 3H), 1.30-1.27 (m, 2H), 1.10 (s, 9H).

Aufarbeitung

  1. customVolotiles were evaporated in vacuo
  2. additionthe residue was diluted with methanol (30 mL)
  3. customthe insoluble inorganic salts were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on silica gel (CH2Cl2/MeOH=20/1 to 5/1)

Quellen und Nachweise

ORD-Eintrag
ord-40771122922846a89c7a0486c0cb24c2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173639B2

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