Potassium tert-butoxide → 5-(6-Bromo-pyridin-2-yl)-5-methyl-morpholin-3-one

HRID 538295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538295
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:12][C:13](=[O:16])[CH2:14]Cl)([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>C(O)(C)(C)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]2([CH3:11])[NH:12][C:13](=[O:16])[CH2:14][O:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 86668009N-[1-(6-bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

Produkt 1

HCID 866680115-(6-Bromo-pyridin-2-yl)-5-methyl-morpholin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of N-[1-(6-bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide in tert-butanol (90 ml) was added KOtBu and the reaction mixture was stirred at rt for 4 h. The reaction mixture was quenched with H2O and diluted with EtOAc. The phases were separated and the aq. phase was twice extracted with EtOAc. The combined org. phases were washed with brine, dried over Na2SO4, filtered and the solvent was removed to leave the title compound as a pale yellow solid. HPLC RtH4=0.73 min; ESIMS: 271, 273 [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.72 (s, 1H), 7.82-7.78 (m, 1H), 7.57-7.51 (m, 2H), 4.10 (d, 2H), 4.00 (d, 1H), 3.65 (d, 1H), 1.42 (s, 3H).

Aufarbeitung

  1. customThe reaction mixture was quenched with H2O
  2. additiondiluted with EtOAc
  3. customThe phases were separated
  4. extractionthe aq. phase was twice extracted with EtOAc
  5. washphases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-0267fa889951467cb4c54739089f6a13
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865712B2

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