1-tert-Butyl-4-piperidone → 1-tert-Butylpiperidin-4-ol

HRID 394155Notes

Reaction equation

HRID 394155 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 738401-tert-Butyl-4-piperidoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 226478821-tert-Butylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of 1.0 g of 1-tert-butylpiperidin-4-one (COMPOUND PPA-1) in 2 mL of THF was added 6.4 mL of a 1M solution of lithium aluminum hydride in THF dropwise. The mixture was stirred 10 min at rt, then quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water. The mixture was stirred vigorously for 30 min, then filtered and concentrated to yield the title compound.

Workup

  1. customquenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water
  2. stirringThe mixture was stirred vigorously for 30 min
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b4104085776a4fe9a158e48d25546ceb
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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