Ethanol → HCID 40428300, compound

HRID 928034Notes

Reaction equation

HRID 928034 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH2:16])[CH2:11]1)(=O)[CH3:8].C(O)C>C1COCC1>[CH2:7]([N:10]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH2:16])[CH2:11]1)[CH3:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 68299941HCID 68299941, compound2×

Product 1

HCID 40428300HCID 40428300, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride was added to a stirred solution of ((R)-1-acetylpyrrolidin-3-ylmethyl)amine (Intermediate 164, 1.5 g) in THF (50 mL) and the resulting mixture was stirred and heated at reflux for 2 hours. After cooling, ethanol was slowly added and the mixture was concentrated under vacuum. The residue was diluted with DCM and the solid was filtered off. The filtrate was evaporated to dryness to give ((R)-1-ethylpyrrolidin-3-ylmethyl)amine (0.9 g) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under vacuum
  5. additionThe residue was diluted with DCM
  6. filtrationthe solid was filtered off
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-4652e69070c848e7b2e52076c3e2eedd
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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