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

HRID 471453ノート

反応式

HRID 471453 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-84a46c380a6343c6a9f110b30d235092
出典データセット
uspto-grants-2014_01
特許番号
US08633182B2

反応ノート

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