Water → (R)-1-Benzyl-3-pyrrolidinol tosylate

HRID 1597324Notes

Reaction equation

HRID 1597324 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.[OH2:25]>N1C=CC=CC=1>[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-:22])(=[O:21])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 86583595(R)-1-Benzyl-3-pyrrolidinol tosylateYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (R)-1-benzyl-3-pyrrolidinol (1.77 g, 10 mmol) in 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, dried(Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c3655ffcebcf46f1b2117edc13c6fb07
Source dataset
uspto-grants-2001_09
Patent number
US06294557B1

Reaction notes

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