Aluminium lithium hydride → 1-(2-Aminoethyl)pyrrolidin-3-ol

HRID 926730Notes

Reaction equation

HRID 926730 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]#[N:15])[CH2:9]1>C1COCC1>[NH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][CH:8]([OH:7])[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 45087269(3S)-3-Hydroxy-1-pyrrolidineacetonitrile

Product 1

HCID 210653341-(2-Aminoethyl)pyrrolidin-3-olYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

1M Solution of LAH in THF (4.38 mL, 4.38 mmol) was added to a solution of (S)-2-(3-hydroxypyrrolidin-1-yl)acetonitrile (Bio. org. Med. Chem. 15 (2007) 5369-538) (460 mg, 3.65 mmol) in THF (15 mL) at −78° C. and allowed the reaction mixture to stir at 25-35° C. for 10 minutes. The reaction mixture was refluxed for 3 h. The reaction mixture was quenched with saturated aqueous sodium sulphate solution at 0° C., heated to reflux, filtered the solid precipitate; filtrate collected was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 250 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customThe reaction mixture was quenched with saturated aqueous sodium sulphate solution at 0° C.
  3. temperatureheated
  4. temperatureto reflux
  5. filtrationfiltered the solid precipitate
  6. customfiltrate collected
  7. dry with materialwas dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6701c4407c8a4b4aa8aed346d8582b73
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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