6-(2-methylpropyl)piperidine-2,4-dione → HCID 66732004, compound

HRID 1963109Notes

Reaction equation

HRID 1963109 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([CH:11]1[NH:16][C:15](=O)[CH2:14][C:13](=[O:18])[CH2:12]1)[CH:8]([CH3:10])[CH3:9]>C1COCC1>[CH2:7]([CH:11]1[CH2:12][CH:13]([OH:18])[CH2:14][CH2:15][NH:16]1)[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 52466806-(2-methylpropyl)piperidine-2,4-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 66732004HCID 66732004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred ice cooled suspension of LAH (16.1 g, 0.414 mol) in THF (100 mL), a solution of 6-isobutyl-piperidine-2,4-dione (14.0 g, 0.083 mol) in THF (100 mL) was added dropwise under N2. The reaction mixture was warmed to room temperature and stirred under N2 for 48 h. The reaction mixture was cooled to 0° C. and quenched with water (16.1 mL), 1 N NaOH (16.1 mL) and water (16.1 mL). The reaction mixture was filtered and the solid was washed with hot THF (100 mL). The filtrate was concentrated to yield 2-isobutyl-piperidin-4-ol as a solid (9 g, crude).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with water (16.1 mL), 1 N NaOH (16.1 mL) and water (16.1 mL)
  3. filtrationThe reaction mixture was filtered
  4. washthe solid was washed with hot THF (100 mL)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8dc02dea70b647bd93facac53becd429
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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