Aluminium lithium hydride → (2R)-1,4-Dimethyl-2-piperazinemethanol

HRID 2262468Notes

Reaction equation

HRID 2262468 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][C@@H:9]1[CH2:21][OH:22])=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][C@@H:9]1[CH2:21][OH:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66583152(R)-1,4-(Di-Boc)-2-(hydroxymethyl)piperazine

Product 1

HCID 28765199(2R)-1,4-Dimethyl-2-piperazinemethanolYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(R)-2-hydroxymethyl-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (6.24 g, 19.7 mmol) was dissolved in THF (10 mL) and cooled to 0° C. 2M LiAlH4 in THF (30.0 mL, 60.0 mmol) was added. The reaction mixture was stirred at reflux for 4 hours and then cooled to 0° C. and quenched with the drop-wise addition of 1M sodium hydroxide solution (20 mL). The reaction mixture was diluted with THF (50 mL), filtered and the filtrate was concentrated in vacuo to give 1,4-dimethyl-(R)-2-hydroxymethyl piperazine (1.77 g, 62%) as a colourless oil which was used without further purification.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled to 0° C.
  3. customquenched with the drop-wise addition of 1M sodium hydroxide solution (20 mL)
  4. additionThe reaction mixture was diluted with THF (50 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c3a00a0ac2d4400caa550c717d34ae65
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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