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

HRID 382296

Reaction equation

HRID 382296 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 a, 0° C. After 90 h stirring it 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. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ether (150 ml)
  3. washThe extract was washed with water brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-11b9882eca8e46be971e9952247d8938
Source dataset
uspto-grants-2001_10
Patent number
US06310061B2

Linked notes

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