Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylate → [1-(2,2-Dimethylpropyl)piperidin-4-yl]methanol

HRID 2192227

Reaction equation

HRID 2192227 reaction equation
[C:1]([N:7]1[CH2:12][CH2:11][CH:10]([C:13](OCC)=[O:14])[CH2:9][CH2:8]1)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 1164515Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21060224[1-(2,2-Dimethylpropyl)piperidin-4-yl]methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

20a (29.5 g, 122 mmol) was dissolved in 200 mL of tetrahydrofuran and cooled to 0° C. Lithium aluminum hydride (s) (10.6 g, 279 mmol) was added slowly and the reaction was allowed to warm to rt and stirred for 24 h. The reaction was quenched by slow addition of sodium sulfate hydrated crystals (Na2SO4.10H2O) until there was no bubbling on addition followed by 20 mL of water. The mixture was filtered through Celite®, and the Celite® washed with diethyl ether. The solvent was removed from the filtrate to provide 20 g (97%) of the desired product as a white solid. 1H NMR (400 MHz, CDCl3).

Workup

  1. temperatureto warm to rt
  2. customThe reaction was quenched by slow addition of sodium sulfate hydrated crystals (Na2SO4.10H2O) until there
  3. additionbubbling on addition
  4. filtrationThe mixture was filtered through Celite®
  5. washthe Celite® washed with diethyl ether
  6. customThe solvent was removed from the filtrate

Sources & evidence

ORD record
ord-8f9be9092dbf4be9889bb6b389d40088
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Linked notes

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