Sodium Hydroxide → HCID 178481285, Verbindung

HRID 1290998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290998
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[N:10]([CH3:16])[CH2:9]2)[CH2:4][CH2:3]1.Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:22]([O:21][C:19]([CH2:18][O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH2:9][N:10]([CH3:16])[C:11](=[O:15])[N:12]([CH3:14])[CH2:13]2)[CH2:6][CH2:7]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 178481284HCID 178481284, Verbindung

Produkt 1

HCID 178481285HCID 178481285, VerbindungAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

trans-5-(4-Hydroxycyclohexyl) -1 , 3-dimethylhexahydro-2-oxo-1,3,5-triazine (1.00 g, 4.40 mmol) and t-butyl bromoacetate (1.29 g, 6.60 mmol) were dissolved in toluene (13 ml), and tetra-n-butylammonium hydrogensulfate (45 mg, 0.13 mmol) was added to the mixture. A solution of sodium hydroxide (13.2 g, 330 mmol) dissolved in water (13.2 ml) was dropwise added, and the mixture was stirred at room temperature for 15 hours. The organic layer was partitioned, washed with water and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to give 680 mg of trans-5-[4-[(t-butoxycarbonyl)methyloxy]cyclohexyl]-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine as a colorless solid (45%).

Aufarbeitung

  1. additionwas dropwise added
  2. customThe organic layer was partitioned
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration, low boiling matters
  6. distillationwere distilled away from the filtrate under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-72e027fbdcd6496b9032a78623550c8e
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753670

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