Ethyl 1-methylpiperidine-4-carboxylate → 1-Methyl-4-piperidinemethanol

HRID 1012123Notes

Reaction equation

HRID 1012123 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:12][N:9]1[CH2:10][CH2:11][CH:6]([CH2:4][OH:3])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 11062856Ethyl 1-methylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2719711-Methyl-4-piperidinemethanolYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of 1-methyl-piperidine-4-carboxylic acid ethyl ester (0.855 g, 5 mmol) in THF (30 ml) was added dropwise a 1M solution of LiAlH4 in THF (20 ml, 20 mmol). The reaction mixture was then stirred for 18 h whilst warming to ambient temperature, and then quenched by careful addition of water (0.75 ml), 10% aqueous NaOH (0.75 ml) then water (3×0.75 ml) and stirred at ambient temperature for 2 h. The resultant mixture was reduced in vacuo, shaken with ethyl acetate and filtered to remove inorganic residues. The filtrate was reduced in vacuo to give (1-methyl-piperidin-4-yl)-methanol as a colourless oil (0.468 g, 73%). (LC/MS: Rt 0.33, [M+H]+ 130.20).

Workup

  1. customquenched by careful addition of water (0.75 ml), 10% aqueous NaOH (0.75 ml)
  2. stirringwater (3×0.75 ml) and stirred at ambient temperature for 2 h
  3. stirringshaken with ethyl acetate
  4. filtrationfiltered
  5. customto remove inorganic residues

Sources & evidence

ORD record
ord-049d078acd874ec48f329e917ca4b936
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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