Water → 1,2,3,6-Tetrahydro-1-methylpyridine-4-methanol

HRID 617736Notes

Reaction equation

HRID 617736 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8](OCC)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[OH:9][CH2:8][C:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 566021Ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1189211,2,3,6-Tetrahydro-1-methylpyridine-4-methanolYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-methyl-1,2,3,6tetrahydro-4-pyridinecarboxylate (10.0 ml, 0.061 mole) in THF (200 ml) was added, maintaining temperature below 25° C., lithium aluminium hydride (2.76 g, 0.073 mole). After stirring for a further 15 min, water (2.75 ml), 10% NaOH (4 ml) and water (4 ml) were successively added, and the mixture was filtered. The filtrate was dried (Na2SO4) and evaporated in vacuo to give the title compound as an amber oil (6.30 g, 81%), which solidified on standing.

Workup

  1. filtrationthe mixture was filtered
  2. dry with materialThe filtrate was dried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-e0115a0524324c4a8ae49617b8f1d989
Source dataset
uspto-grants-1999_09
Patent number
US05952325

Reaction notes

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