Reaktion #837161

Reaktionsgleichung

(R)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

4-hydroxydiphenylamine

NaH

→

title product

Ausbeute 73.0%

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

Ausbeute 73.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was warmed to it
2. 2
   Temperaturheated at 90° C. for 15 h
3. 3
   EinengenThe mixture was concentrated
4. 4
   workup.ADDITIONdiluted with saturated aq NaHCO3
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   ExtraktionThe aqueous layer was re-extracted with ethylacetate
7. 7
   SonstigeThe combined organic layers were dried over anhy
8. 8
   SonstigeMgSO4 and the solvent was removed in vacuo
9. 9
   Sonstigeto obtain the crude mixture, which
10. 10
    Sonstigewas purified by silica gel flash chromatography

Vorschrift

To a solution of 4-hydroxydiphenylamine (200 mg, 1.08 mmol) in DMF (3 mL) at 0-5° C. was added 60% NaH (80 mg, 2 mmol) at 0-5° C. The reaction mixture was stirred at rt for 15 min at 0-5° C. A solution of (R)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (387 mg, 1.09 mmol) in DMF (2 mL) was added to the above mixture at 0-5° C. The reaction mixture was warmed to it and then heated at 90° C. for 15 h. The mixture was concentrated, diluted with saturated aq NaHCO3 and extracted with ethyl acetate. The aqueous layer was re-extracted with ethylacetate. The combined organic layers were dried over anhy. MgSO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the title product (289 mg, 73%).

Quelle