Tetrabutylammonium Fluoride → (2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one

HRID 627160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627160
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[CH:7]=[CH:8][C@H:9]2[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[CH:7]=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 89851884(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one2×

Produkt 1

HCID 89852367(2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 129, 1.64 g, 5.05 mmol) in THF (40 mL), tetrabutylammonium fluoride (6.06 ml, 6.06 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. The mixture was concentrated and purified by silica gel column (40 g, 50-100% Hex/EA) to give the desired product (1.03 g) as an yellow oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel column (40 g, 50-100% Hex/EA)

Quellen und Nachweise

ORD-Eintrag
ord-8142ed1dcc6a45a089fbc71a9af96d94
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

Notizen zur Reaktion

Wird geladen…