Diisopropylethylamine → (R)-3-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1094255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094255
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1.CCN(C(C)C)C(C)C.CC(=O)OCC.CCCCCCC>CCO.CC(=O)OCC>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:19]2[N:20]=[CH:21][C:16]([Br:15])=[CH:17][N:18]=2)[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 21899848Ethylacetate heptane

Produkt 1

HCID 66639558(R)-3-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-amino-1-N-Boc-piperidine (920 mg) in dry EtOH (20 mL) were added successively 5-bromo-2-chloropyrimidine (957 mg), DIEA (0.86 mL). The reaction mixture was stirred at reflux for 16 hours under nitrogen. After cooling to RT, the reaction mixture was diluted with EA, washed with sat. NaHCO3, 1N NaOH. The organic extract was dried (MgSO4), filtered and concentrated to yield a crude brown-orange oil. FC (EA/n-heptane: 2/8) gave 787 mg (48%) of the title compound as a light brown solid.

Aufarbeitung

  1. temperatureat reflux for 16 hours under nitrogen
  2. washwashed with sat. NaHCO3, 1N NaOH
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude brown-orange oil

Quellen und Nachweise

ORD-Eintrag
ord-bc11a06f67ad407e8f83f67990e20913
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133901B2

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