Methanesulfonyl chloride → (3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

(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).

1. temperatureThe reaction mixture is cooled to 0° C.
2. customto reach room temperature
3. stirringAfter stirring for 2 h
4. concentrationthe reaction mixture is concentrated under vacuum, water
5. additionis added
6. extractionthe reaction mixture is extracted with ethyl acetate
7. customThe organic phase is collected
8. dry with materialdried over sodium sulfate
9. customseparated
10. concentrationconcentrated under vacuum
11. customThe crude product obtained
12. customis triturated with a solution of cyclohexane/dichloromethane 1:1

ORD record

ord-84a46c380a6343c6a9f110b30d235092

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633182B2