Reaktion #329728

Reaktionsgleichung

1-t-butoxycarbonyl-3-pyrrolidinone

4-chlorophenyl magnesium bromide

→

1-t-butoxycarbonyl-3-(4-chlorophenyl)-3-hydroxypyrrolidine

Ausbeute 60.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen quenched by the addition of saturated aqueous NH4OH (8 mL)
2. 2
   ExtraktionThe aqueous layer was extracted with EtOAc (50 mL×2)
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeChromatographic purification on silica gel (Hexane/EtOAc=3/1)

Vorschrift

To a stirred solution of 1-t-butoxycarbonyl-3-pyrrolidinone (0.57 g, 3.23 mmol) in THF (10 mL) was added 4-chlorophenyl magnesium bromide (1.0 M, 5.2 mL) under the protection of argon at 0° C. The reaction was stirred at room temperature for 1 hour then quenched by the addition of saturated aqueous NH4OH (8 mL). The aqueous layer was extracted with EtOAc (50 mL×2), dried over MgSO4 and concentrated in vacuo. Chromatographic purification on silica gel (Hexane/EtOAc=3/1) provided 0.57 g 1-t-butoxycarbonyl-3-(4-chlorophenyl)-3-hydroxypyrrolidine (60%). m/z 298 (m+1)

Quelle