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

HRID 374552

Reaction equation

HRID 374552 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

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 at room temperature for two days, water is added, and the aqueous phase is separated off and extracted with toluene. The toluene solutions are washed with 10% strength hydrochloric acid, dried over magnesium sulphate, concentrated, dissolved in ethyl acetate and filtered through silica gel. The filtrate is concentrated.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted with toluene
  3. washThe toluene solutions are washed with 10% strength 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

Sources & evidence

ORD record
ord-e6a0c98000a042158049382407c2f051
Source dataset
uspto-grants-1996_01
Patent number
US05480879

Linked notes

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