Water → HCID 86324392, compound

HRID 928062Notes

Reaction equation

HRID 928062 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][C:15]#[N:16])[CH2:10]1)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][NH2:16])[CH2:10]1)[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86713361HCID 86713361, compound2×

Product 1

HCID 86324392HCID 86324392, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.0 g) was added in portions to a stirred, cooled solution of 2-((S)-1-ethylpyrrolidin-3-yl)acetonitrile (Intermediate 204, 3.8 g) in THF (20 mL) at 0° C. On completion of the addition, the mixture was stirred at room temperature for 4 hours. Water was added cautiously, followed by addition of 15% aqueous sodium hydroxide solution and more water. The solid was filtered off and the filtrate was evaporated to dryness. The residue was dissolved in DCM, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 2-((R)-1-ethylpyrrolidin-3-yl)ethylamine (2.0 g) as a colourless oil, which was used without further characterisation.

Workup

  1. additionOn completion of the addition
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in DCM
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6bde3980e309426a9840fb483e36cf9d
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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