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Sodium Bicarbonate → HCID 59397846, Verbindung

HRID 2193184
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2193184
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH:13]=O.[C:15]([O:19][C:20](=[O:39])[N:21]([CH2:28][C:29]1[CH:38]=[CH:37][C:32]2[O:33][CH2:34][CH2:35][O:36][C:31]=2[CH:30]=1)[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([CH3:18])([CH3:17])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C.ClCCl>[C:15]([O:19][C:20](=[O:39])[N:21]([CH2:28][C:29]1[CH:38]=[CH:37][C:32]2[O:33][CH2:34][CH2:35][O:36][C:31]=2[CH:30]=1)[CH:22]1[CH2:27][CH2:26][N:25]([CH2:13][CH2:12][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[CH:11][C:2]2=[O:1])[CH2:24][CH2:23]1)([CH3:18])([CH3:16])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 17781681(2-oxoquinolin-1(2H)-yl)acetaldehydeHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate

Produkt 1

HCID 59397846HCID 59397846, VerbindungAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 5 mL of dichloromethane solution containing 0.15 g of (2-oxoquinolin-1(2H)-yl)acetaldehyde, 0.27 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate, 45 μL of acetic acid and 0.25 g of sodium triacetoxyborohydride were added and stirred for 4 hours. To the reaction mixture, water and ethyl acetate were added, neutralized with aqueous saturated sodium hydrogen carbonate solution, thereafter the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=100:1], to give 0.13 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow oil.

Aufarbeitung

  1. additionwere added
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washwashed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=100:1]

Quellen und Nachweise

ORD-Eintrag
ord-484f6378e0644092bac98ca0753db815
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329694B2

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