Reaktion #558635

Reaktionsgleichung

(S)-3-Hydroxypyrrolidine

DIPEA

methanesulfonyl chloride

→

title compound

Methanesulfonic acid (S)-1-methanesulfonyl-pyrrolidin-3-yl ester

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is cooled to 0° C.
2. 2
   Sonstigeto reach room temperature
3. 3
   workup.STIRRINGAfter stirring for 2 h
4. 4
   Einengenthe reaction mixture is concentrated under vacuum, water
5. 5
   workup.ADDITIONis added
6. 6
   Extraktionthe reaction mixture is extracted with ethyl acetate
7. 7
   SonstigeThe organic phase is collected
8. 8
   Trocknendried over sodium sulfate
9. 9
   Sonstigeseparated
10. 10
    Einengenconcentrated under vacuum
11. 11
    SonstigeThe crude product obtained
12. 12
    Sonstigeis triturated with a solution of cyclohexane/dichloromethane 1:1

Vorschrift

(S)-3-Hydroxypyrrolidine (2 g, 23 mmol) is dissolved in 40 mL of tetrahydrofuran. DIPEA (10 mL, 57.36 mmol) is added and the reaction mixture is stirred for 30 min at room temperature. The reaction mixture is cooled to 0° C., methanesulfonyl chloride (3.73 mL, 48.21 mmol) is added dropwise and the reaction mixture is allowed to reach room temperature. After stirring for 2 h, the reaction mixture is concentrated under vacuum, water is added and the reaction mixture is extracted with ethyl acetate. The organic phase is collected, dried over sodium sulfate, separated and concentrated under vacuum. The crude product obtained is triturated with a solution of cyclohexane/dichloromethane 1:1 to give the title compound. (Yield: 2.2 g).

Quelle