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Triethylamine → 2-(2-Fluoro-4-(trifluoromethyl)phenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963222
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1963222
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH:16]([C:18]([O:20]C)=[O:19])[CH2:15][CH2:14][N:13]1[C:22]([O:24][CH3:25])=[O:23].[Br-].[Li+].CCN(CC)CC.CC(OC)(C)C>C(#N)C.O>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH:16]([C:18]([OH:20])=[O:19])[CH2:15][CH2:14][N:13]1[C:22]([O:24][CH3:25])=[O:23]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66735134Dimethyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate

Produkt 1

HCID 667315582-(2-Fluoro-4-(trifluoromethyl)phenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acidAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dimethyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (5.33 g, 14.67 mmol) was dissolved in acetonitrile (35 mL) and water (0.700 mL), then lithium bromide (10.19 g, 117.37 mmol) was added. Et3N (8.18 mL, 58.68 mmol) was added and the resulting yellow suspension was heated under reflux for 1 h. Water (50 mL) and MTBE (150 mL) were added. The phases were separated and the organic layer was extracted with water (2 times). The pooled water layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE (2 times). The combined organic layer was dried over Na2SO4, filtered and evaporated yielding 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.82 g, 94%) as a slightly yellow solid. MS m/z 348 (M−H)−

Aufarbeitung

  1. temperaturethe resulting yellow suspension was heated
  2. temperatureunder reflux for 1 h
  3. customThe phases were separated
  4. extractionthe organic layer was extracted with water (2 times)
  5. extractionextracted with MTBE (2 times)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-27d29b41274142fa90ad2593346f530e
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415378B2

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