Sodium sulfate decahydrate → (2S)-2-(tetrahydro-2H-pyran-4-ylmethyl)piperazine

HRID 1972343Notes

Reaction equation

HRID 1972343 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C@@H:8]2[NH:13][C:12](=O)[CH2:11][NH:10][C:9]2=O)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[O:1]1[CH2:2][CH2:3][CH:4]([CH2:7][C@H:8]2[CH2:9][NH:10][CH2:11][CH2:12][NH:13]2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 66582474(3S)-3-(tetrahydro-2H-pyran-4-ylmethyl)-2,5-piperazinedione

Product 1

HCID 66582396(2S)-2-(tetrahydro-2H-pyran-4-ylmethyl)piperazineYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250-mL round-bottomed flask was charged with (3S)-3-(tetrahydro-2H-pyran-4-ylmethyl)-2,5-piperazinedione (1.44 g, 6.78 mmol), 50 mL of THF, and LAH (1M in THF, 27.1 mL, 27.1 mmol, Sigma-Aldrich, St. Louis, Mo.). After heating at reflux for 2 h, the mixture was allowed to cool to room temperature. Sodium sulfate decahydrate (10 g) was then added and the mixture was stirred at temperature for 1 h. The mixture was filtered and the filtrate was concentrated to give (2S)-2-(tetrahydro-2H-pyran-4-ylmethyl)piperazine (0.950 g, 5.16 mmol) as a colorless oil.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2551b4ab4ac847b88ce08d421ff06ded
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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