Sodium Azide → 3-Azidomethyl-2-(5-bromopyridin-3-yl)-2-azabicyclo[3.1.0]hexane

HRID 241602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241602
CS(O[CH2:6][CH:7]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CC1C=COC=1C.CCOCC>[N:20]([CH2:6][CH:7]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1)=[N+:21]=[N-:22]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 866749142-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-ylmethyl methanesulfonate

Produkt 1

HCID 711149553-Azidomethyl-2-(5-bromopyridin-3-yl)-2-azabicyclo[3.1.0]hexaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 343372,3-DimethylfuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of methane sulfonate (as obtained in Step (i) of Example 1) (215 mg, 0.62 mmol) in dry dimethylfuran (2 mL) was added sodium azide (180 mg, 2.77 mmol). The reaction mixture was gradually heated to 90° C. and stirred for 16 hours. Upon completion of the reaction, it was diluted with ether, washed with water, brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography to obtain the title compound as gummy liquid of 164 mg. Yield: 90%.

Aufarbeitung

  1. customUpon completion of the reaction, it
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-787b1c2a609141ca87f2385f22b1179f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653071B2

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