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Hydrochloric Acid → (2S, 4R)-1-(4-Toluenesulfonyl)-2-(chloromethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine

HRID 1614343
ノート
印刷プレビュー

反応式

HRID 1614343 の反応式
O[CH2:2][C@H:3]1[CH2:7][C@H:6]([OH:8])[CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.[ClH:30]>N1C=CC=CC=1.C(O)C>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([N:4]2[CH2:5][C@H:6]([O:8][S:25]([C:22]3[CH:21]=[CH:20][C:19]([CH3:29])=[CH:24][CH:23]=3)(=[O:26])=[O:27])[CH2:7][C@H:3]2[CH2:2][Cl:30])(=[O:11])=[O:10])=[CH:13][CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 15629267(3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

生成物 1

HCID 15629275(2S, 4R)-1-(4-Toluenesulfonyl)-2-(chloromethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine収率 70%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 1049
Pyridine
溶媒

反応条件

温度
50 °C

実験手順

To an ice-cold solution of 170 g (626.5 mmol) of (2R, 4S)-2-hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine in 0.5 l of pyridine was added 250 g (1.32 mol) of p-toluenesulfonyl chloride in one portion and the reaction was warmed to 50° C. After 6 hours the mixture was cooled with an ice bath and 3 l of 10% aqueous hydrogen chloride solution was carefully added. A white precipitate formed which was isolated via filtration and then taken in 1 l of ethanol and heated to reflux for 30 minutes. The mixture was then cooled and the solids were filtered and dried under reduced pressure to give 195 g of product in 70% yield. M.P.=145°-146° C.

後処理

  1. temperatureAfter 6 hours the mixture was cooled with an ice bath
  2. customA white precipitate formed which
  3. customwas isolated via filtration
  4. temperatureheated
  5. temperatureto reflux for 30 minutes
  6. temperatureThe mixture was then cooled
  7. filtrationthe solids were filtered
  8. customdried under reduced pressure

出典と根拠

ORDレコード
ord-104a453b7e224051b79ad299bd68d2fa
出典データセット
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05196548

反応ノート

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