Reaktion #1513482

Reaktionsgleichung

di-tert-butyl azodicarboxylate

triphenylphosphine

3-bromo-5-fluorophenol

tert-butyl 4-hydroxypiperidine-1-carboxylate

→

desired product

Ausbeute 70.0%

tert-butyl 4-(3-bromo-5-fluorophenoxy)piperidine-1-carboxylate

Ausbeute 70.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed
2. 2
   workup.DISSOLUTIONthe residue was dissolved in methanol
3. 3
   Sonstigepurified by preparative-LCMS (C18 column
4. 4
   Wascheneluting with a gradient of ACN/H2O containing 0.15% NH4OH)

Vorschrift

To a mixture of triphenylphosphine (1.75 g, 6.66 mmol) and 3-bromo-5-fluorophenol (795 mg, 4.16 mmol) and tert-butyl 4-hydroxypiperidine-1-carboxylate (922 mg, 4.58 mmol) in THF (20. mL) was added di-tert-butyl azodicarboxylate (1.53 g, 6.66 mmol) (DBAD) at 0° C. The reaction was stirred overnight at room temperature. The solvent was removed and the residue was dissolved in methanol and purified by preparative-LCMS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) to give the desired product (1.09 g, 70%). LCMS (M+Na)+: 396.0, 398.0.

Quelle