Imidazole → (S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

HRID 340928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340928
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:14]([O:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Produkt 1

HCID 10263224(S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-oneAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-(hydroxymethyl)pyrrolidin-2-one (30.0 g, 261 mmol) and imidazole (23.1 g, 340 mmol) in DCM (900 mL) was added TBS-Cl (42.9 g, 288 mmol). The reaction mixture was stirred at RT for 30 min and filtered. The filtrate was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one (50 g, 83.7%). LRMS (M+H+) m/z 230.2.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on silica gel column
  7. additiona mixture of EtOAc and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-28d440d014cd423fb3f5ad8a4e06d6f9
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895582B2

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