5-Hexenal → 5-(Hex-5-enyl)-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 517934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517934
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[C:8]1([CH3:31])[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]3[CH2:30][CH2:29][CH2:28][NH:27][C:17]3=[N:18][C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[CH:10][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH2:1]([N:27]1[C:17]2=[N:18][C:19]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([CH3:31])=[CH:9][CH:10]=3)[N:15]=[C:16]2[CH2:30][CH2:29][CH2:28]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Komponenten

5

Edukt 3

HCID 698175-HexenalHCID 5049666Sodium triacetoxyborohydrideHCID 666645252,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Produkt 1

HCID 896901775-(Hex-5-enyl)-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Hex-5-enal (step 1) (solution in DCM, 25 mmol) was treated with 2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate B) (3.94 g, 12.5 mmol). After stirring at room temp under nitrogen for 30 mins, sodium triacetoxyborohydride (3.18 g, 15.00 mmol) was added and stirring continued at room temperature overnight. Water (100 ml) was added to the reaction mixture. Once effervescence had ceased the organic portion was separated and dried by passing through a phase separating column. The solvent was removed under reduced pressure and the resulting brown oil was purified by flash column chromatography on silica eluting with 0-100% EtOAc in iso-hexane on a 80 g silca cartridge. The combined fractions were allowed to stand at room temperature for 2 days. The resulting suspension was collected by filtration and dried in a vacuum oven. The crude material was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound;

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at room temperature overnight
  3. customwas separated
  4. customdried
  5. customseparating column
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting brown oil was purified by flash column chromatography on silica eluting with 0-100% EtOAc in iso-hexane on a 80 g silca cartridge
  8. waitto stand at room temperature for 2 days
  9. filtrationThe resulting suspension was collected by filtration
  10. customdried in a vacuum oven
  11. customThe crude material was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-edce6f0f2fef4903b8f706d4cf5308d4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115129B2

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