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

HRID 129427Notes

Reaction equation

HRID 129427 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. 60 g (0.31 mol) of tosyl chloride in 450 ml of toluene are added dropwise. The batch is stirred two days at room temperature, water is added, and the aqueous phase separated and extracted with toluene. The toluene solutions are washed with 10% hydrochloric acid, dried over magnesium sulfate, concentrated, dissolved in ethyl acetate, and filtered through silica gel. The filtrate is concentrated.

Workup

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

Sources & evidence

ORD record
ord-de50d233c30d4834a316e8d12f24762f
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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