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Water → rac-tert-butyl 7,8-dihydroxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 406265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 406265
[Mn]([O-])(=O)(=O)=O.[K+].[C:7]1([C:13]2[N:14]=[C:15]3[CH:28]=[CH:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:16]3=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(=O)(O)[O-:37].[Na+].[OH2:41]>[Cl-].C([N+](CCCC)(CCCC)C)CCC.C(Cl)Cl>[OH:41][CH:27]1[CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:16]2=[N:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:14]=[C:15]2[CH:28]1[OH:37]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 66665728tert-Butyl 2,3-diphenylpyrido[2,3-b]pyrazine-5(6H)-carboxylate

Produkt 1

HCID 66665861rac-tert-butyl 7,8-dihydroxy-2,3-diphenyl-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 (728 mg, 3.09 mmol) in DCM (10 ml) was added potassium permanganate (488 mg, 3.09 mmol) portionwise over 10 minutes at room temperature. The reaction mixture was allowed to stir under an atmosphere of nitrogen for 30 minutes. The mixture was cooled down to 0° C. and treated dropwise with a solution of tert-butyl 2,3-diphenylpyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 1)(700 mg, 1.816 mmol) in DCM (8 ml). The reaction was then left to stir for a further 2 hours at 0-5° C. under an atmosphere of nitrogen. A solution of sodium bisulfite (1134 mg, 10.90 mmol) in water (9 ml) was added dropwise at 0-5° C. to the reaction mixture. The mixture was filtered through Celite® (filter material) and washed with DCM (20 ml) and water (10 ml). The organic layer was separated and concentrated in vacuo to give a foamy solid. The crude material was purified by chromatography on silica eluting with 0-90% EtOAc/iso-hexane to afford the title compound;

Aufarbeitung

  1. waitThe reaction was then left
  2. stirringto stir for a further 2 hours at 0-5° C. under an atmosphere of nitrogen
  3. filtrationThe mixture was filtered through Celite® (filter material)
  4. washwashed with DCM (20 ml) and water (10 ml)
  5. customThe organic layer was separated
  6. concentrationconcentrated in vacuo
  7. customto give a foamy solid
  8. customThe crude material was purified by chromatography on silica eluting with 0-90% EtOAc/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-8be91d0087e74c798c1514bef2d2f9cd
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754085B2

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