Reaktion #453100

Reaktionsgleichung

DEAD

196d

3-bromo-5-hydroxy-2-methylpyridine

1-BOC-2-(S)-azetidinemethanol

diethylazodicarboxylate

Triphenylphosphine

→

3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-methyl-pyridine

Ausbeute 70.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturto warm slowly to ambient temperature
3. 3
   Sonstigethe solvent was evaporated
4. 4
   Sonstigethe crude residue was chromatographed (silica gel; hexanes/EtOAc, 4:1)
5. 5
   Sonstigeto provide an oil

Vorschrift

Triphenylphosphine (6.3 g, 24 mmol) was dissolved in THF (100 mL), cooled to 0° C. and treated with diethylazodicarboxylate (3.8 mL, 24 mmol) for 15 min. Then the compound of 196d (3 g, 16 mmol) followed by 1-BOC-2-(S)-azetidinemethanol (3.4 g, 18 mmol) was added and the reaction was allowed to warm slowly to ambient temperature. After 3 days, the solvent was evaporated and the crude residue was chromatographed (silica gel; hexanes/EtOAc, 4:1) to provide an oil. The product was contaminated with a byproduct related to the DEAD reagent and was taken forward as is; the subsequent allowed isolation of the byproduct and revealed ~35 wt % contamination therefor the calculated yield was 70% (4.0 g, 11.2 mmol): TLC Rf 0.6 (1:1 hexanes/EtOAc); MS (CI/NH3) m/z 357 (M+H)+.

Quelle