Water → 3-(Pyrid-3-yl)-3-(2-hydroxyethyl)pyrrolidine

HRID 323334Notes

Reaction equation

HRID 323334 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][C:15](=O)[NH:14][CH2:13]1)C.O.[OH-].[Na+]>O1CCCC1.CO.ClCCl>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:12]2([CH2:11][CH2:10][OH:9])[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:19]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22009411(3-(Pyrid-3-yl)-5-oxo-pyrrolidin-3-yl)acetic acid ethyl ester

Product 1

HCID 184650333-(Pyrid-3-yl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

Combine lithium aluminum hydride (4.0 g, 105 mmol) and anhydrous tetrahydrofuran (200 mL). Slowly, add a solution of (3-(pyrid-3-yl)-5-oxo-pyrrolidin-3-yl)acetic acid ethyl ester (13.0 g, 52.4 mmol) in anhydrous tetrahydrofuran (100 mL). After the addition is complete, heat to reflux. After 4 hours, cool in an ice-bath. Add water (4 mL) dropwise at such a rate that the temperature of the reaction mixture does not rise above 20° C. Cool to 10° C., add 2 M aqueous sodium hydroxide solution (4.0 mL). Add water (16 mL) and stir. After 16 hours, filter the reaction mixture and concentrate the filtrate in vacuo to give an aqueous layer. Extract with dichloromethane and lyophilize the aqueous layer to give a residue. Combine the residue and dichloromethane and methanol. Filter and evaporate the filtrate in vacuo to give the title compound.

Workup

  1. additionAfter the addition
  2. temperatureheat to reflux
  3. temperaturecool in an ice-bath
  4. customdoes not rise above 20° C
  5. waitAfter 16 hours
  6. filtrationfilter the reaction mixture
  7. concentrationconcentrate the filtrate in vacuo
  8. customto give an aqueous layer
  9. extractionExtract with dichloromethane
  10. customto give a residue
  11. filtrationFilter
  12. customevaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-0a7a9ab7f3694077950b9395a47a750f
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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