Tetrabutylammonium Fluoride → HCID 22242912, Verbindung

HRID 891681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891681
[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:15][CH:14]([O:16][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:13][CH:14]([OH:16])[CH2:15]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 222427721-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine

Produkt 1

HCID 22242912HCID 22242912, VerbindungAusbeute 109,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine (5.31 g, 11.1 mmol) (obtained as described in Reference Example 41(1)) in anhydrous tetrahydrofuran (266 ml) was added a solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (13.3 ml, 13.3 mmol) in an ice bath. The mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (2.91 g, yield 100%) as pale brown crystals.

Aufarbeitung

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-9ee825e39fcc4d7c9ba9131204c3dec5
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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