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Ethyl Acetate → tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate

HRID 75105
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 75105
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[N:3][CH:4]=1
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Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 27364342-Bromo-5-(trifluoromethyl)pyridine

Produkt 1

HCID 58576452tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 0.678 g (3 mmol) of 2-bromo-5-(trifluoromethyl)pyridine, 0.901 g (4.5 mmol) of tert-butyl 4-aminopiperidine-1-carboxylate and 0.829 g (6 mmol) of potassium carbonate in 5 ml of dimethyl sulphoxide is heated at 100° C. for 20 hours. The mixture is cooled to ambient temperature and then 50 ml of ethyl acetate and 15 ml of water are added. The organic phase is separated by settling and washed twice with 15 ml of water and then with 15 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated under vacuum. The product is purified by chromatography on silica gel, elution being carried out with a 20:80 and then 30:70 mixture of ethyl acetate and cyclohexane in order to obtain 0.864 g (2.5 mmol) of product in the form of a white solid.

Aufarbeitung

  1. temperatureThe mixture is cooled to ambient temperature
  2. customThe organic phase is separated
  3. washwashed twice with 15 ml of water
  4. dry with materialIt is dried over sodium sulphate
  5. customevaporated under vacuum
  6. customThe product is purified by chromatography on silica gel, elution
  7. addition30:70 mixture of ethyl acetate and cyclohexane in order

Quellen und Nachweise

ORD-Eintrag
ord-9d9fb918e31e49c8ae43b43b85cd4bb9
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835418B2

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