Water → 4-(Pyrrolidin-1-yl)butan-1-ol

HRID 1387081Notes

Reaction equation

HRID 1387081 reaction equation
O=[C:2]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5](O)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[N:8]1([CH2:2][CH2:3][CH2:4][CH2:5][OH:6])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 8538084-Oxo-4-(pyrrolidin-1-yl)butanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 131719524-(Pyrrolidin-1-yl)butan-1-olYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Oxo-4-(1-pyrrolidinyl)butyric acid (0.30 g; 1.75 mmol) in 10 mL of THF in an argon-filled flask was treated with lithium aluminum hydride (0.17 g; 4.38 mmol) at 70° C. for 4 h. After cooling the mixture to room temperature, hydrolysis was effected by addition of 0.17 mL each of water and 5 N NaOH, followed by 0.51 mL of water. Stirring was continued for 0.5 h. The mixture was filtered and concentrated under reduced pressure to give the title compound as a colorless oil (0.21 g; 84% yield).

Workup

  1. customhydrolysis
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39381958b6b74e25966ee8c17828ba85
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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