Di-tert-butyl dicarbonate → [2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amine

HRID 2099710

Reaktionsgleichung

Reaktionsgleichung von HRID 2099710
Br.[CH2:2]([NH:4][CH:5]([CH3:15])[CH2:6][C:7]1[CH:8]=[C:9]([OH:14])[C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:3].[C:16](=[O:19])(O)[O-].[Na+].[C:21](O[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(OC(C)(C)C)=O>O.C1COCC1>[CH3:21][O:14][C:9]1[CH:8]=[C:7]([CH2:6][CH:5]([NH:4][CH2:2][CH3:3])[CH3:15])[CH:12]=[CH:11][C:10]=1[O:19][CH3:16].[C:32]([O:31][C:29](=[O:30])[N:4]([CH:5]([CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)[CH2:2][CH3:3])([CH3:33])([CH3:34])[CH3:35]

Komponenten

7

Edukt 3

HCID 90495Di-tert-butyl dicarbonateHCID 1303564-(2-(Ethylamino)propyl)-1,2-benzenediol hydrobromideHCID 516892Sodium Bicarbonate

Produkt 2

HCID 22061570[2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amineHCID 70986816HCID 70986816, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To all of 2B from the above reaction mixture was added 30 mL of 50% THF in water. To the reaction mixture 1.1 g of sodium bicarbonate was added as a solid followed by 1.35 g (6.18 mmol) of di-t-butyl dicarbonate in 7 mL of THF dropwise over a period of 30 minutes. The reaction mixture was allowed to stir at room temperature for 18 hours, then concentrated under reduced pressure. This was diluted with 50 mL of water and the pH of the solution was adjusted to 5. The aqueous layer was extracted with 3×100 mL of ethyl acetate. The organic layers were combined, dried (anhydrous Na2SO4) and concentrated to dryness. The residue was purified by silica gel column chromatography using 30% ethyl acetate in hexane to give 764 mg (2.58 mmol, 53% from 2A) of 2C as a clear gum (M+Na, 318).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThis was diluted with 50 mL of water
  3. extractionThe aqueous layer was extracted with 3×100 mL of ethyl acetate
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f2f5e5f550ac45f092d8012c30aa23a3
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569676B2

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