Ethanol → (S)-2-(1-Ethylpyrrolidin-2-yl)ethanamine

HRID 928011Notes

Reaction equation

HRID 928011 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[CH2:9][C:10]#[N:11])(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C>C1COCC1>[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[CH2:9][CH2:10][NH2:11])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 45085914(S)-2-(1-Acetylpyrrolidin-2-yl)acetonitrile2×

Product 1

HCID 14447348(S)-2-(1-Ethylpyrrolidin-2-yl)ethanamineYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

((S)-1-Acetylpyrrolidin-2-yl)acetonitrile (Intermediate 137, 1.0 g) was added portionwise to a stirred, cooled solution of lithium aluminium hydride (0.36 g) in THF (30 mL) under an atmosphere of nitrogen while maintaining the temperature at 0° C. The mixture was allowed to warm to room temperature then heated at reflux for 2 hours. After cooling, ethanol (4 mL) was added dropwise and the resultant solid was filtered off. The filtrate was evaporated to dryness to give 2((S)-1-ethylpyrrolidin-2-yl)ethylamine (0.6 g) as a colourless oil.

Workup

  1. temperatureto warm to room temperature
  2. temperaturethen heated
  3. temperatureat reflux for 2 hours
  4. temperatureAfter cooling
  5. filtrationthe resultant solid was filtered off
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f0f0e7cac4f54c029f4d6eb8275c789e
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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