Potassium tert-butoxide → 2-(5-Bromo-pyridin-2-yl)-8-oxa-2-aza-spiro[4.5]decan-1-one

HRID 2401116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401116
C[O:2][C:3]([C:5]1([CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[CH2:12][CH2:11][C:5]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[C:3]2=[O:2])=[N:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 674786784-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

Produkt 1

HCID 674786592-(5-Bromo-pyridin-2-yl)-8-oxa-2-aza-spiro[4.5]decan-1-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(5-bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester in THF (15 mL) was added a solution of potassium t-butoxide (1 M in THF) (3.5 eq), and allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (15 mL), quenched with brine (2 mL). The aqueous layer was extracted with ethyl acetate (2×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. Purification over silica gel eluting with methanol in dichloromethane (0-10%) afforded 0.4 g (46%) of title compound.

Aufarbeitung

  1. customquenched with brine (2 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customPurification over silica gel eluting with methanol in dichloromethane (0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-d14f1fb0bed9481c937e7e3e4a1e30a9
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796278B2

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