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Water → rac-Tert-butyl 7,8-dihydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 406200
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 406200
[Mn]([O-])(=O)(=O)=O.[K+].[C:7]1([CH3:37])[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:29]=[CH:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:16]3=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:9][CH:8]=1.S(=O)(O)[O-:39].[Na+].[OH2:43]>[Cl-].C([N+](CCCC)(CCCC)C)CCC.C(Cl)Cl>[OH:43][CH:28]1[CH2:27][N:26]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[C:16]2=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([CH3:37])=[CH:12][CH:11]=3)[N:14]=[C:15]2[CH:29]1[OH:39]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 66666278tert-Butyl 2,3-dip-tolylpyrido[2,3-b]pyrazine-5(6H)-carboxylate

Produkt 1

HCID 66665909rac-Tert-butyl 7,8-dihydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 91822Tributylmethylammonium chlorideKatalysator
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tributylmethylammonium chloride (0.970 g, 4.11 mmol) in DCM (15 ml) at RT under nitrogen was added potassium permanganate (0.650 g, 4.11 mmol) portionwise over 10 minutes. The mixture was cooled to 0° C. and treated dropwise with a solution of tert-butyl 2,3-dip-tolylpyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2) (1 g, 2.418 mmol) in DCM (10 ml). A solution of sodium bisulfite (1.510 g, 14.51 mmol) in water (12.5 ml) was added keeping the temperature <10° C. The mixture was filtered through Celite® (filter material), washing with DCM. The phases were separated and the organic portion was washed with brine, dried (sodium sulphate), filtered and the solvent was removed in vacuo. The crude product was dissolved in DCM and purified by chromatography on silica eluting with 30-50% EtOAc in iso-hexanes to afford the title compound;

Aufarbeitung

  1. customthe temperature <10° C
  2. filtrationThe mixture was filtered through Celite® (filter material)
  3. washwashing with DCM
  4. customThe phases were separated
  5. washthe organic portion was washed with brine
  6. dry with materialdried (sodium sulphate)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. dissolutionThe crude product was dissolved in DCM
  10. custompurified by chromatography on silica eluting with 30-50% EtOAc in iso-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5e2b1906b94441489d4cd006247cd8ce
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754085B2

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