Lithium pyrrolidinoborohydride → 9-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid

HRID 517897

Reaktionsgleichung

Reaktionsgleichung von HRID 517897
O=[C:2]1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH2:4][CH2:3]1.N1([BH3-])CCCC1.[Li+]>C1COCC1>[C:14]1([CH3:17])[CH:13]=[CH:12][C:11]([C:9]2[N:10]=[C:5]3[CH2:4][CH2:3][CH2:2][N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:6]3=[N:7][C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 23697345Lithium pyrrolidinoborohydrideHCID 716576499-(6-Oxo-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid

Produkt 1

HCID 896898969-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

9-(6-Oxo-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid (Example 8) (200 mg, 0.412 mmol) in THF (10 ml) was stirred under N2 for 10 mins. Lithium pyrrolidinoborohydride (1M in THF) (2.059 ml, 2.059 mmol) was added carefully and the resulting mixture was stirred at RT for 1.5 hours. The reaction was quenched with 1M HCl and the mixture was concentrated under reduced pressure. The resulting mixture was extracted with DCM and the organic extracts were passed through a phase separating column. The organics were concentrated under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the titled compound;

Aufarbeitung

  1. customThe reaction was quenched with 1M HCl
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionThe resulting mixture was extracted with DCM
  4. customseparating column
  5. concentrationThe organics were concentrated under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-52b9509e4b13464eba5333f3799fc174
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115129B2

Verknüpfte Notizen

Wird geladen…