Sodium Sulfate → 2-(Pyrrolidin-1-ylmethyl)pyrrolidine

HRID 369884Notes

Reaction equation

HRID 369884 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:12]([CH:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[N:7]1([CH2:12][CH:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 550904Pyrrolidin-1-yl(pyrrolidin-2-yl)methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1428252-(Pyrrolidin-1-ylmethyl)pyrrolidineYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (9 g) is suspended in dry tetrahydrofuran (100 ml) under ice-cooling, and thereto is added dropwise a solution of 2-(1-pyrrolidinyl)carbonylpyrrolidine (33 g) in dry tetrahydrofuran (80 ml). The mixture is refluxed under nitrogen atmosphere for four hours. The mixture is cooled with ice, and thereto is added a saturated aqueous sodium sulfate solution (about 15 ml), and then mixture is further stirred at room temperature for three hours. The precipitated sodium sulfate is removed by filtration, washed well with chloroform. The filtrate and the washings are combined, concentrated under reduced pressure, and evaporated to give 2-(1-pyrrolidinyl)methylpyrrolidine (22 g).

Workup

  1. temperaturecooling
  2. temperatureThe mixture is refluxed under nitrogen atmosphere for four hours
  3. temperatureThe mixture is cooled with ice
  4. customThe precipitated sodium sulfate is removed by filtration
  5. washwashed well with chloroform
  6. concentrationconcentrated under reduced pressure
  7. customevaporated

Sources & evidence

ORD record
ord-c1131094427749b29a96b4a0c315abbb
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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