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

HRID 538295Notes

Reaction equation

HRID 538295 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0267fa889951467cb4c54739089f6a13
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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