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

HRID 1614343
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HRID 1614343 반응식
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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 1049
Pyridine
용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-104a453b7e224051b79ad299bd68d2fa
출처 데이터셋
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05196548

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