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

HRID 471453노트

반응식

HRID 471453 반응식
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>O1CCCC1>[CH3:16][S:17]([N:4]1[CH2:5][CH2:6][C@H:2]([O:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:3]1)(=[O:19])=[O:18]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-ol

생성물 1

HCID 59816083(3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-84a46c380a6343c6a9f110b30d235092
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633182B2

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