HCID 18318541, compound → 1-Methylpyrrolidine-3-ethanol

HRID 2259711Notes

Reaction equation

HRID 2259711 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([CH3:15])[C:11]1=O>>[CH3:15][N:12]1[CH2:13][CH2:14][CH:10]([CH2:9][CH2:8][OH:7])[CH2:11]1

Participants

3

Reactant 2

HCID 18318541HCID 18318541, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 211911231-Methylpyrrolidine-3-ethanolYield 52.9%

Procedure

Lithium aluminium hydride (347 mg) was cautiously added, in portions, to a vigorously stirred suspension of 3-(2-hydroxyethyl)-1-methyl-2-pyrrolidinone (886 mg) in dry, freshly distilled tetrahydrofuran (60 ml), at 5° under nitrogen. The resultant suspension was stirred and heated at reflux under nitrogen for 1 h. The mixture was cooled to 5°, with stirring, and cautiously treated with a mixture of water (1 ml) and tetrahydrofuran (10 ml). The solvents were evaporated, the residue dissolved in ethanol and the solvent was again removed, in vacuo. The residue was chromatographed using dichloromethane:ethanol:ammonia (25.8:1) as eluent, to give the title compound (423 mg).

Workup

  1. customin dry
  2. customat 5°
  3. temperatureheated
  4. temperatureat reflux under nitrogen for 1 h
  5. temperatureThe mixture was cooled to 5°
  6. stirringwith stirring
  7. additioncautiously treated with a mixture of water (1 ml) and tetrahydrofuran (10 ml)
  8. customThe solvents were evaporated
  9. dissolutionthe residue dissolved in ethanol
  10. customthe solvent was again removed, in vacuo
  11. customThe residue was chromatographed

Sources & evidence

ORD record
ord-193a23b0d3e44245abee774810cb5e87
Source dataset
uspto-grants-1995_12
Patent number
US05475020

Reaction notes

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