Sodium Azide → (S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

HRID 1845122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845122
[O:1]1[CH2:3][C@H:2]1[C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[N:8][CH:9]=1.Cl([O-])(=O)(=O)=O.[Li+].[N-:20]=[N+:21]=[N-:22].[Na+]>C(#N)C>[N:20]([C@@H:2]([C:4]1[CH:9]=[N:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)[CH2:3][OH:1])=[N+:21]=[N-:22]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 23665649Lithium perchlorateHCID 581880495-[(2R)-oxiran-2-yl]-2-(trifluoromethyl)pyridine

Produkt 1

HCID 58188243(S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of (R)-5-(oxiran-2-yl)-2-(trifluoromethyl)pyridine (2.72 g, 14.4 mmol) in acetonitrile (200 mL) were added lithium perchlorate (20 g, 0.19 mol) and sodium azide (3.7 g, 57 mmol). The mixture was stirred at 60° C. overnight and TLC indicated completion of the reaction. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was treated with water and extracted with EtOAc. The combined organic layers were dried, and concentrated. The residue was purified by silica gel column to afford the title compound.

Aufarbeitung

  1. customcompletion of the reaction
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. additionThe residue was treated with water
  6. extractionextracted with EtOAc
  7. customThe combined organic layers were dried
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-682a5483668f44a180b39332bf9f274c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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