Aluminium lithium hydride → [1-(2,6-Dimethylphenyl)piperidin-3-yl]methanol

HRID 2426743Notes

Reaction equation

HRID 2426743 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[N:15]1[C:20](=O)[CH2:19][CH2:18][C:17]([C:22](OC)=[O:23])=[CH:16]1>>[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:22][OH:23])[CH2:16]1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67250551Methyl 1-(2,6-dimethylphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate

Product 1

HCID 57422589[1-(2,6-Dimethylphenyl)piperidin-3-yl]methanol

Procedure

In an atmosphere of nitrogen, a 1.0 M diisobutylaluminum hydride THF solution was dropwise added at −78° C. to a THF solution of methyl 1-(2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate. After stirring at −78° C. for 2 hours, the temperature was risen to 0° C., followed by stirring at 0° C. for 1.5 hours. The reaction mixture was warmed up to room temperature, followed by stirring at room temperature for 2 hours. A 1.0 M diisobutylaluminum hydride THF solution was dropwise added to the reaction mixture at 0° C., followed by warming up to room temperature and stirring for 1 hour to obtain methyl 1-(2,6-dimethylphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate. In an atmosphere of nitrogen, lithium aluminum hydride was added to the resulting methyl 1-(2,6-dimethylphenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate, while cooling on an ice-methanol bath. Thereafter, by stirring the reaction mixture for 2 hours while heating under reflux, [1-(2,6-dimethylphenyl)piperidin-3-yl]methanol was obtained.

Workup

  1. temperaturewhile cooling on an ice-methanol bath
  2. temperaturewhile heating
  3. temperatureunder reflux

Sources & evidence

ORD record
ord-b3e3fa116c9547d086a9d2f1115bf478
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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