Water → (1-Benzylpyrrolidin-3-yl)methanol

HRID 1682004Notes

Reaction equation

HRID 1682004 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](O)=[O:14])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 225602101-Benzyl-2-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

35 g (0.16 mol) of N-benzyl-2-pyrrolidone-3-carboxylic acid dissolved in 250 ml of absolute tetrahydrofuran is added dropwize, with stirring, to 12.2 g (0.32 mol) of lithium aluminium hydride in 350 ml of absolute tetrahydrofuran. After refluxing for 6 hours, 18.2 ml of water, 12.2 ml of 15% sodium hydroxide solution and 36.6 ml of water are added, whilst cooling with ice water. The precipitate formed is suction filtered and washed with tetrahydrofuran. The combined filtrates are concentrated by evaporation in vacuo and the residue obtained is purified over 900 g of aluminium oxide (neutral, activity II) with methylene chloride and then with increasing amounts of ethanol (up to 2%). Yield: 16 g (52.3% of theory), Rf value: 0.42 (aluminium oxide, neutral, eluant: 5% ethanol in methylene chloride).

Workup

  1. additionis added dropwize
  2. temperatureAfter refluxing for 6 hours
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with tetrahydrofuran
  6. concentrationThe combined filtrates are concentrated by evaporation in vacuo
  7. customthe residue obtained
  8. customis purified over 900 g of aluminium oxide (neutral, activity II) with methylene chloride

Sources & evidence

ORD record
ord-4884815dbab846b885a1505ce7a3e325
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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