Water → 1-Benzyl-3-aminopyrrolidine

HRID 1165568Notes

Reaction equation

HRID 1165568 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][CH:8]1[CH2:12][C:11](=O)[N:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]1=O.O.[OH-].[K+]>O1CCCC1>[NH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 434308HCID 434308, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 27566131-Benzyl-3-aminopyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

34 g (0.9 mol) of lithium aluminum hydride are initially introduced under nitrogen in 500 ml of anhydrous tetrahydrofuran, and 80.8 g (0.4 mol) of 3-amino-1-benzylpyrrolidine-2,5-dione are added dropwise to the mixture as a solution in 400 ml of tetrahydrofuran. The mixture is then refluxed for 20 hours. 34 g of water in 120 ml of tetrahydrofuran, 34 g of 10% strength potassium hydroxide solution and also 136 g of water are added dropwise in succession to the mixture. The solid is filtered off with suction, washed with THF, thoroughly boiled in 250 ml of tetrahydrofuran and again filtered off with suction. The combined filtrates are concentrated in a rotary evaporator, and the residue is distilled under reduced pressure.

Workup

  1. temperatureThe mixture is then refluxed for 20 hours
  2. filtrationThe solid is filtered off with suction
  3. washwashed with THF
  4. filtrationagain filtered off with suction
  5. concentrationThe combined filtrates are concentrated in a rotary evaporator
  6. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-adc6994fcada47748c47528dd1cda81d
Source dataset
uspto-grants-1990_03
Patent number
US04910319

Reaction notes

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