Sodium triacetoxyborohydride → HCID 58579385, Verbindung

HRID 657030

Reaktionsgleichung

Reaktionsgleichung von HRID 657030
CO[CH:3](O)[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:17].CC([N:23]([C@@H:27]1[CH2:32][CH2:31][NH:30][CH2:29][C@@H:28]1[OH:33])[C:24](=[O:26])[O-:25])(C)C.OCC[CH2:37][C:38]1[C:43](=O)N(CC2C=CC(OC)=CC=2)NC(=O)[CH:39]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.CO>[OH:33][C@@H:28]1[C@H:27]([NH:23][C:24](=[O:26])[O:25][C:38]([CH3:43])([CH3:39])[CH3:37])[CH2:32][CH2:31][N:30]([CH2:3][CH2:4][N:5]2[C:14]3[C:9](=[N:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=3)[CH:8]=[CH:7][C:6]2=[O:17])[CH2:29]1

Komponenten

7

Edukt 4

HCID 5049666Sodium triacetoxyborohydrideHCID 675265645-(3-Hydroxypropyl)-1-{[4-(methyloxy)phenyl]methyl}-1,2-dihydro-3,6-pyridazinedioneHCID 86635329[7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde methyl hemiacetalHCID 866353341,1-dimethylethyl[(3S,4R)-3-hydroxy-4-piperidinyl]carbamate

Produkt 1

HCID 58579385HCID 58579385, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

[7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde methyl hemiacetal (200 mg) and 1,1-dimethylethyl[(3S,4R)-3-hydroxy-4-piperidinyl]carbamate (for a synthesis see WO2004058144, Example 5(c), cis-(3-hydroxy-piperidin-4-yl)-carbamic acid tert-butyl ester Enantiomer 2) (182 mg) were stirred in chloroform (10 ml) plus MeOH (0.5 ml) under argon for 2 h. Sodium triacetoxyborohydride (534 mg) was added in one portion and the mixture was stirred at rt overnight, then quenched by addition of saturated aqueous sodium hydrogen cabonate (2 ml). The organic phase was separated using a hydrophobic frit and the aqueous phase was extracted with DCM (2×20 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica, eluted with 0-20% (2M ammonia in MeOH) in DCM. Appropriate fractions were combined and evaporated under reduced pressure to give the title compound (226 mg) as an off-white foam.

Aufarbeitung

  1. customquenched by addition of saturated aqueous sodium hydrogen cabonate (2 ml)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with DCM (2×20 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give the crude product, which
  8. customwas purified by column chromatography on silica
  9. washeluted with 0-20% (2M ammonia in MeOH) in DCM
  10. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75413877429d4323a4ccab5fb04d673c
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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