Water → trans-1-Benzoyl-3-bromo-4-(2-tosyloxyethoxy)-pyrrolidine

HRID 1648478

반응식

HRID 1648478 반응식
[C:1]([N:9]1[CH2:13][C@@H:12]([O:14][CH2:15][CH2:16][OH:17])[C@H:11]([Br:18])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:1]([N:9]1[CH2:13][C@@H:12]([O:14][CH2:15][CH2:16][O:17][S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C@H:11]([Br:18])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67598706trans-1-Benzoyl-3-bromo-4-(2-hydroxyethoxy)-pyrrolidine

생성물 1

HCID 86748810trans-1-Benzoyl-3-bromo-4-(2-tosyloxyethoxy)-pyrrolidine

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매2회

실험 절차

92 g (0.239 mol) of trans-1-benzoyl-3-bromo-4-(2-hydroxyethoxy)-pyrrolidine, 32 g (0.316 mol) of triethylamine and 1 g of 4-dimethylaminopyridine are dissolved in 750 ml of toluene, and 60 g (0.31 mol) of tosyl chloride in 450 ml of toluene are added dropwise. The mixture is stirred for two days at room temperature, water is added, and the aqueous phase is separated off and extracted with toluene. The toluene solutions are washed with 10% hydrochloric acid, dried over magnesium sulphate, concentrated, dissolved in ethyl acetate and filtered through silica gel. The filtrate is concentrated.

후처리

  1. customthe aqueous phase is separated off
  2. extractionextracted with toluene
  3. washThe toluene solutions are washed with 10% hydrochloric acid
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. dissolutiondissolved in ethyl acetate
  7. filtrationfiltered through silica gel
  8. concentrationThe filtrate is concentrated

출처 및 근거

ORD 기록
ord-9cf0aab62be145fab4018f9ec9e68165
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436334

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