Reaktion #170104

Reaktionsgleichung

DEAD

Phenol

triphenylphosphine

tert-butyl 3-hydroxypyrrolidine-1-carboxylate

tert-Butyl 3-hydroxypyrrolidine-1-carboxylate

→

title compound

Ausbeute 25.0%

tert-Butyl 3-phenoxypyrrolidine-1-carboxylate

Ausbeute 25.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONthen diluted with dichloromethane
4. 4
   Filtrationfiltered
5. 5
   WaschenThe filtrate was washed three times with NaOH 0.2N and brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenthen concentrated
8. 8
   SonstigeThe residue was purified on column chromatography (eluent: pentane EtOAc 9/1)

Vorschrift

Phenol (503 mg, 5.34 mmol) and triphenylphosphine (1.40 g, 5.34 mmol) were added to a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol; which may be prepared as described in Step 1) in anhydrous THF (13 mL) under nitrogen. The reaction mixture was cooled to 0° C. and DEAD (775 μL, 4.27 mmol) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure then diluted with dichloromethane and filtered. The filtrate was washed three times with NaOH 0.2N and brine, dried over Na2SO4 then concentrated. The residue was purified on column chromatography (eluent: pentane EtOAc 9/1) to give the title compound (175 mg, 25%) as a yellow oil.

Quelle