Pyrrolidine → HCID 68692826, compound

HRID 13775Notes

Reaction equation

HRID 13775 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>C(O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 10471906Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl ester

Product 1

HCID 68692826HCID 68692826, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

2.00 g of (R)-1-benzyl-3-(p-toluenesulfonyloxy)pyrrolidine (J. Med. Chem., 1992, 35, 4205-4208) was dissolved in 12 ml of ethanol, 1.63 g of pyrrolidine was added, and then the mixture was stirred at 140° C. for 20 hours in a sealed tube. The reaction solution was concentrated under reduced pressure, mixed with water, followed by extraction with ethyl acetate, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.97 g of the objective compound as a brown oily product.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionmixed with water
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f30451cf738345dd942d1704a5674f1a
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Reaction notes

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