Reacción #41200

Ecuación de reacción

(R)-Boc-prolinol tosylate

p-benzyloxy phenol

NaH

→

crystals

Rendimiento 55.6%

2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Rendimiento 55.6%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe resulting reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   TemperaturaIt was then cooled to −5° C.
4. 4
   workup.ADDITIONadded dropwise to the reaction mixture
5. 5
   Temperaturato warm to rt
6. 6
   workup.STIRRINGstirred at 92° C. for 5 h and at rt overnight
7. 7
   workup.STIRRINGstirred for an hour
8. 8
   FiltraciónThe resulting precipitate was filtered
9. 9
   Lavadowashed with ether
10. 10
    Secadodried over MgSO4
11. 11
    Concentraciónconcentrated
12. 12
    Otrorecrystallized with ether/hexane

Procedimiento

To a 15 mL of anhydrous DMF was added NaH (60% dispersion in oil, 338 mg, 8.44 mmol), and the resulting reaction mixture was cooled to 0° C. p-benzyloxy phenol (1.41 g, 7.03 mmol) was added and the reaction mixture was stirred at rt for 45 min. It was then cooled to −5° C., and (R)-Boc-prolinol tosylate (2.5 g, 7.03 mmol) in anhydrous DMF (5 mL) was cooled in a separate ice-bath and added dropwise to the reaction mixture. It was then allowed to warm to rt and stirred at 92° C. for 5 h and at rt overnight. The resulting mixture was poured into 200 mL ice/water and stirred for an hour. The resulting precipitate was filtered, washed with ether, dried over MgSO4, concentrated, recrystallized with ether/hexane to give shiny yellow crystals (1.5 g, 55%).

Fuente