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

HRID 1741029Notes

Reaction equation

HRID 1741029 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-1,2,3,6-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.

Workup

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

Sources & evidence

ORD record
ord-823f859d789948c288d2eff8a90c7fd7
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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