Imidazole → (S)-2-[2-(tert-butyl-dimethyl-silyloxy)-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1963060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963060
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][C@@H:22]1[CH2:27][CH2:28][OH:29])=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][C@@H:22]1[CH2:27][CH2:28][O:29][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12046236(S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

Produkt 1

HCID 67773623(S)-2-[2-(tert-butyl-dimethyl-silyloxy)-ethyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Tert-butyl-dimethyl-silyl chloride (3.62 g, 24.02 mmol) and imidazole (3.27 g, 48.03 mmol) were added to a solution of the compound of step 2 (4.609 g, 20.01 mmol) in 75 ml of DCM and the resulting solution was stirred at room temperature for 3 h. The mixture was washed with 50 ml of water and then 50 ml of brine. The aqueous phase was extracted once with DCM. The combined organic phases were dried over sodium sulfate, filtered and evaporated under reduced pressure to give 6.90 g of the title compound as a pale yellow oil.

Aufarbeitung

  1. washThe mixture was washed with 50 ml of water
  2. extractionThe aqueous phase was extracted once with DCM
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-27cf665530d9482a841b79e0fbebd370
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415336B2

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