Sodium triacetoxyborohydride → HCID 21073484, Verbindung

HRID 1373648

Reaktionsgleichung

Reaktionsgleichung von HRID 1373648
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1.[CH2:18]1[C:26]2[C:21](=[C:22]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20][O:19]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH2:18]1[C:26]2[C:21](=[C:22]([N:27]3[CH2:32][CH2:31][N:30]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]4[N:9]=[C:10]5[C:5]([CH:4]=[CH:3][C:2](=[O:1])[NH:11]5)=[CH:6][CH:7]=4)[CH2:29][CH2:28]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20][O:19]1

Komponenten

6

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 210731161-(1,3-Dihydro-isobenzofuran-4-yl)-piperazineHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Produkt 1

HCID 21073484HCID 21073484, VerbindungAusbeute 15,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.257 g, 1.107 mmol, 1.1 eq) and 1-(1,3-dihydro-isobenzofuran-4-yl)-piperazine (0.204 g, 0.998 mmol, 1 eq) in dichloroethane (5 mL) was added NaBH(OAc)3 (0.433 g, 2.043 mmol, 1.84 eq). The slurry was allowed to stir overnight at room temperature (18 h). The mixture was diluted with EtOAc and quenched with saturated NaHCO3. The organic phase was then washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Purification by silica gel chromatography (2% MeOH/CH2Cl2) followed by formation of the HCl salt using 1N HCl in ether provided the title compound (0.064 g, 12%). CHN Found: C, 64.37; H, 6.54; N, 12.13. This calculates out for C24H28N4O3×0.74HCl.

Aufarbeitung

  1. customquenched with saturated NaHCO3
  2. washThe organic phase was then washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by silica gel chromatography (2% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-383d6aa6824949e8889bbddd14698469
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160888B2

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