Reaktion #357290

Reaktionsgleichung

tert-Butyl 3-oxopyrrolidine-1-carboxylate

trimethyl(trifluoromethyl)silane

tetrabutylammonium fluoride

→

subtitled compound

tert-Butyl 3-hydroxy-3-(trifluoromethyl)pyrrolidine-1-carboxylate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice-bath was removed
2. 2
   workup.ADDITIONSaturated aqueous NH4Cl solution (8 mL) was added
3. 3
   workup.STIRRINGstirring
4. 4
   workup.ADDITIONAfter 15 min TBAF (2.36 g TBAF in 7.5 mL THF) was added
5. 5
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1 h
6. 6
   ExtraktionThe reaction mixture was extracted with ethyl acetate
7. 7
   Waschenwashed with H2O
8. 8
   Trocknendried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum spirit)

Vorschrift

tert-Butyl 3-oxopyrrolidine-1-carboxylate (926 mg, 5.0 mmol) was dissolved in THF (10 mL) and the solution was cooled to 0° C., trimethyl(trifluoromethyl)silane (0.872 mL) and tetrabutylammonium fluoride (TBAF) (176 mg, 0.557 mmol) were added. The ice-bath was removed and the reaction mixture was stirred at room temperature overnight. Saturated aqueous NH4Cl solution (8 mL) was added and stirring was continued. After 15 min TBAF (2.36 g TBAF in 7.5 mL THF) was added and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was extracted with ethyl acetate, washed with H2O, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum spirit) to give the subtitled compound (800 mg).

Quelle