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

HRID 381735

Reaction equation

HRID 381735 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 86583595(R)-1-Benzyl-3-pyrrolidinol tosylateYield 175.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-83b8f201dfb748bdafa93b0432845b9a
Source dataset
uspto-grants-2001_10
Patent number
US06307061B2

Linked notes

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