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Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate → Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

HRID 661232
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 661232
[F:1][C:2]([F:21])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:19]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1>C(O)(=O)C.[Pd].[Pt](=O)=O>[F:21][C:2]([F:1])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][NH:12][CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19]2)=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 58116526Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate

Produkt 1

HCID 58116537Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator3×HCID 345198Adams' catalystKatalysator3×HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 9.20 g (23.4 mmol, purity 75%) of the compound from Example 52A in concentrated acetic acid (192 ml) was admixed with 1.94 g of palladium/carbon (10% palladium) and 2.23 g of platinum (IV) oxide. This was followed by hydrogenation under a hydrogen atmosphere at standard pressure for 6 h, then addition of another 1.00 g of palladium/carbon (10% palladium) and 2.00 g of platinum(IV) oxide, and hydrogenation under a hydrogen atmosphere at standard pressure overnight. Subsequently, a further 1.00 g of palladium/carbon (10% palladium) and 3.00 g of platinum(IV) oxide were added, and hydrogenation was effected under a hydrogen atmosphere at standard pressure for a further 24 h. The reaction solution was filtered through Celite, the filter residue was washed with methanol/water and the combined filtrates were concentrated under reduced pressure. The residue was taken up in dichloromethane and then washed with a 1 N aqueous sodium carbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 6.64 g (85% of theory, purity 90%)

Aufarbeitung

  1. waithydrogenation was effected under a hydrogen atmosphere at standard pressure for a further 24 h
  2. filtrationThe reaction solution was filtered through Celite
  3. washthe filter residue was washed with methanol/water
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. washwashed with a 1 N aqueous sodium carbonate solution
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7550aa4b5f054b88be12b4954801d5b4
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084469B2

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