Imidazole → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 564923

Reaktionsgleichung

Reaktionsgleichung von HRID 564923
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].N1C=CN=C1.[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.O>[Si:11]([O:5][CH2:4][CH2:3][NH:2][CH3:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 80162-(Methylamino)ethanolHCID 94078tert-Butyldiphenylchlorosilane

Produkt 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-methylethanolamine (600 mg), in N,N-dimethylformamide were added imidazole (1.13 g) and tert-butyldiphenylsilyl chloride (2.20 g) at ambient temperature with stirring. After 8 hours, the mixture was diluted with water (60 ml) and was extracted with ethyl acetate (20 ml) twice. The organic layer was washed with water three times and brine, dried over magnesium sulfate. The solvent was removed in vacuo. The residue was purified by column chromatography eluting with dichloromethane-methanol to give N-(2-tert-butyldiphenylsilyloxyethyl)-N-methylamine (780 mg) as an oil.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate (20 ml) twice
  2. washThe organic layer was washed with water three times and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with dichloromethane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-12efae263eca4be991f2e94a41bf1af9
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169095A

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