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]=1Participants
6
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
- filtrationthe mixture was filtered
- dry with materialThe filtrate was dried (Na2SO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-e0115a0524324c4a8ae49617b8f1d989
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952325
Reaction notes
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