Water → HCID 86748810, Verbindung

HRID 129427

Reaktionsgleichung

Reaktionsgleichung von HRID 129427
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 86748810HCID 86748810, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-de50d233c30d4834a316e8d12f24762f
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468742

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