Benzyl Alcohol → Benzyl[2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxan-5-yl]carbamate

HRID 64445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64445
[CH3:1][C:2]1([CH3:17])[O:7][CH2:6][C:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)(C(O)=O)[CH2:4][O:3]1.[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P([N:40]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:43](=[O:46])([O-])O.[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:18]([O:25][C:43](=[O:46])[NH:40][C:5]1([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:4][O:3][C:2]([CH3:1])([CH3:17])[O:7][CH2:6]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 4

HCID 244Benzyl AlcoholHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 900723352,2-Dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylic acid

Produkt 1

HCID 131737220Benzyl[2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxan-5-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 1.09 g of 2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylic acid were added 20 ml of toluene, 0.9 ml of triethylamine, 2.4 ml of benzyl alcohol, and 1.3 ml of diphenylphosphoryl azide, followed by stirring at 100° C. for 17 hours. After leaving to be cooled, to the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.01 g of benzyl[2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxan-5-yl]carbamate.

Aufarbeitung

  1. customAfter leaving
  2. temperatureto be cooled, to the reaction mixture
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fe6a8b4c99004640842e478e34fded6d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

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