Citric Acid → (3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate

HRID 2280652ノート

反応式

HRID 2280652 の反応式
Cl.[OH:2][C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[CH3:15][S:16]([O:2][C@H:3]1[CH2:7][CH2:6][N:5]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:4]1)(=[O:18])=[O:17]

参加物

6

反応物 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22309122(S)-3-Hydroxypyrrolidine hydrochloride

生成物 1

HCID 59816083(3S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate収率 62.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

The crude (S)-3-hydroxyl-pyrrolidine hydrochloride 11b (124 mg, 1 mmol) was dissolved in 15 mL of dichloromethane, followed by addition of triethylamine (303 mg, 3 mmol). The reaction solution was cooled down to 0° C., followed by addition of methanesulfonyl chloride (264 mg, 2.30 mmol), then warmed up to room temperature and stirred for another 2.5 hours. The resulting solution was mixed with 10 mL of dichloromethane, 1M citric acid was added dropwise to adjust the pH to 4˜5, the organic phase was dried with anhydrous magnesium sulphate and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (S)-1-(methylsulfonyl)pyrrolidin-3-yl methanesulfonate 11c (153 mg) as a yellow solid, which was directly used in the next step without further purification.

後処理

  1. temperaturewarmed up to room temperature
  2. additionwas added dropwise
  3. dry with materialthe organic phase was dried with anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4da8a0012f1642619cb96cd2ffb31fad
出典データセット
uspto-grants-2015_09
特許番号
US09139548B2

反応ノート

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