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

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

Reactant 4

HCID 962Water2×

HCID 14798Sodium Hydroxide

HCID 566021Ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate

HCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

Procedure

To a solution of ethyl 1-methyl-1,2,3,6-tetrahydro-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.