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Triethylamine → 2-(3-tert-Butylphenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963152
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1963152
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]2[CH2:16][CH:15]([C:17]([O:19]C)=[O:18])[CH2:14][CH2:13][N:12]2[C:21]([O:23][CH3:24])=[O:22])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]2[CH2:16][CH:15]([C:17]([OH:19])=[O:18])[CH2:14][CH2:13][N:12]2[C:21]([O:23][CH3:24])=[O:22])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734775Dimethyl 2-(3-tert-butylphenyl)piperidine-1,4-dicarboxylate

Produkt 1

HCID 667322282-(3-tert-Butylphenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dimethyl 2-(3-tert-butylphenyl)piperidine-1,4-dicarboxylate (3.17 g, 9.51 mmol) was dissolved in acetonitrile (60 mL) and water (1.200 mL), then lithium bromide (6.61 g, 76.06 mmol) was added in one portion. Triethylamine (5.27 mL, 38.03 mmol) was added and the resulting brown suspension was heated under reflux for 1.5 h. Water (120 mL) and MTBE (120 mL) were added. The organic phase was extracted with water (2×25 mL). The pooled aqueous layer was acidified to pH 1 with 0.5 M HCl (30 mL) and extracted with MTBE (2×150 mL). The combined organic layer was washed with water (25 mL), dried over Na2SO4 and evaporated. 2-(3-tert-Butylphenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.73 g, 90%) was isolated as a foam.

Aufarbeitung

  1. temperaturethe resulting brown suspension was heated
  2. temperatureunder reflux for 1.5 h
  3. extractionThe organic phase was extracted with water (2×25 mL)
  4. extractionextracted with MTBE (2×150 mL)
  5. washThe combined organic layer was washed with water (25 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7428f93141a949cc9b9a48ac957ad47b
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415378B2

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