4-Toluenesulfonyl chloride → (R)-1-Benzyl-3-pyrrolidinol tosylate

HRID 381735

Reaktionsgleichung

Reaktionsgleichung von HRID 381735
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>O>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)([O-:13])(=[O:22])=[O:21]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Produkt 1

HCID 86583595(R)-1-Benzyl-3-pyrrolidinol tosylateAusbeute 175,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of (R)1-benzyl-3-pyrrolidinol (1.77 g, 10 mmol) pyridine(30 ml) was added p-toluenesulfonyl chloride (9.53 g, 50 mmol) by portions at 0° C. After 90 h stirring at room temperature, water was added to the reaction mixture and the mixture was extracted with ether (150 ml). The extract was washed with water brine, dried (Na2SO4), and concentrated to give 3.06 g (92%) of brown oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ether (150 ml)
  2. washThe extract was washed with water brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-83b8f201dfb748bdafa93b0432845b9a
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307061B2

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